(1R,2R)-2,3-dihydro-1H-indene-1,2-diol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C., and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1-amino-2-indanol (1.02 g, 63% yield). The mixture was gradually warmed to 20° C. and aged to 3 hours the mixture heated to reflux The resulting solid was removed by filtration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 40 ml of acetonitrile, 3.0 g (20.1 mmol) of trans-(-)-1,2-indandiol (I': trans-configuration: 98.0%; cis-configuration: 2.0%; optical purity: 100% e.e.) was dissolved. At room temperature, 3.2 g (31.7 mmol) of 97% sulfuric acid was dropwise added thereto in a period of 30 minutes. After the resulting mixture was stirred at room temperature for 1 hour, the compound (I') disappeared from an HPLC. To the reaction liquid, 20 ml of water was added. Immediately thereafter, the mixture was heated and 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure. Then, the mixture was subjected to a reflux for 1.5 hours to complete the reaction. The reaction liquid was cooled to room temperature and washed twice with 10 ml of dichloromethane. Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide. The grayish white scaly crystal deposited thereby was filtered off under reduced pressure, washed with a small quantity of water, and then dried under reduced pressure to yield 1.77 g of cis-(-)-1-aminoindan-2-ol (V) as a primary crystal. Then, the mother liquid after the deposition of the crystal was extracted with dichloromethane and the extracted phase was concentrated to yield 0.69 g of the compound (V) as a secondary crystal. optical purity: 100% e.e.) was dissolved was added Immediately thereafter, the mixture was heated 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure a reflux for 1.5 hours the reaction The reaction liquid was cooled to room temperature washed twice with 10 ml of dichloromethane Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide The grayish white scaly crystal deposited thereby was filtered off under reduced pressure washed with a small quantity of water dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 40 ml of acetonitrile, 3.0 g (20.1 mmol) of trans-(-)-1,2-indandiol (I': trans-configuration: 98.0%; cis-configuration: 2.0%; optical purity: 100% e.e.) was dissolved. At room temperature, 3.2 g (31.7 mmol) of 97% sulfuric acid was dropwise added thereto in a period of 30 minutes. After the resulting mixture was stirred at room temperature for 1 hour, the compound (I') disappeared from an HPLC. To the reaction liquid, 20 ml of water was added. Immediately thereafter, the mixture was heated and 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure. Then, the mixture was subjected to a reflux for 1.5 hours to complete the reaction. The reaction liquid was cooled to room temperature and washed twice with 10 ml of dichloromethane. Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide. The grayish white scaly crystal deposited thereby was filtered off under reduced pressure, washed with a small quantity of water, and then dried under reduced pressure to yield 1.77 g of cis-(-)-1-aminoindan-2-ol (V) as a primary crystal. Then, the mother liquid after the deposition of the crystal was extracted with dichloromethane and the extracted phase was concentrated to yield 0.69 g of the compound (V) as a secondary crystal. optical purity: 100% e.e.) was dissolved was added Immediately thereafter, the mixture was heated 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure a reflux for 1.5 hours the reaction The reaction liquid was cooled to room temperature washed twice with 10 ml of dichloromethane Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide The grayish white scaly crystal deposited thereby was filtered off under reduced pressure washed with a small quantity of water dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 100 ml four-neck flask, 4.48 g (30.3 mmol) of trans-(±)-1,2-indandiol (I') and 40 ml of acetonitrile were introduced. This mixture was suspended. While this suspension was stirred at room temperature, 6.14 g (60.6 mmol) of 97% sulfuric acid was added thereto at room temperature in a period of 20 minutes. The temperature within the mixture increased from 19° C. to 35° C. The slurry was completely dissolved to form a slightly yellow transparent solution. The solution was stirred at 24° C. for 1 hour and then at 60° C. for 1 hour. An HPLC analysis of the contents revealed that 70.8% of cis-oxazoline derivative (IV: R=CH3) had been generated, while no trans-amide derivative (III': R=CH3, Y=OH) was detected. Then, 30 ml of water was added thereto and the resulting mixture was stirred at 60° C. for 3 hours. Acetonitrile was removed by azeotropic distillation. The remaining mixture was washed with dichloromethane and then subjected to liquid separation. When an aqueous solution of 25% sodium hydroxide was added to the water phase, a crystal deposited. This crystal was filtered off under reduced pressure, washed with water, and then dried to yield 2.70 g (yield: 59.7%) of cis-(±)-1-aminoindan-2-ol (V) as a white crystal. Its purity determined by an HPLC was 97.7%. The temperature within the mixture increased from 19° C. to 35° C The slurry was completely dissolved to form a slightly yellow transparent solution The solution was stirred at 24° C. for 1 hour at 60° C. for 1 hour the resulting mixture was stirred at 60° C. for 3 hours Acetonitrile was removed by azeotropic distillation The remaining mixture was washed with dichloromethane subjected to liquid separation When an aqueous solution of 25% sodium hydroxide was added to the water phase This crystal was filtered off under reduced pressure washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 100 ml four-neck flask, 4.48 g (30.3 mmol) of trans-(±)-1,2-indandiol (I') and 40 ml of acetonitrile were introduced. This mixture was suspended. While this suspension was stirred at room temperature, 6.14 g (60.6 mmol) of 97% sulfuric acid was added thereto at room temperature in a period of 20 minutes. The temperature within the mixture increased from 19° C. to 35° C. The slurry was completely dissolved to form a slightly yellow transparent solution. The solution was stirred at 24° C. for 1 hour and then at 60° C. for 1 hour. An HPLC analysis of the contents revealed that 70.8% of cis-oxazoline derivative (IV: R=CH3) had been generated, while no trans-amide derivative (III': R=CH3, Y=OH) was detected. Then, 30 ml of water was added thereto and the resulting mixture was stirred at 60° C. for 3 hours. Acetonitrile was removed by azeotropic distillation. The remaining mixture was washed with dichloromethane and then subjected to liquid separation. When an aqueous solution of 25% sodium hydroxide was added to the water phase, a crystal deposited. This crystal was filtered off under reduced pressure, washed with water, and then dried to yield 2.70 g (yield: 59.7%) of cis-(±)-1-aminoindan-2-ol (V) as a white crystal. Its purity determined by an HPLC was 97.7%. The temperature within the mixture increased from 19° C. to 35° C The slurry was completely dissolved to form a slightly yellow transparent solution The solution was stirred at 24° C. for 1 hour at 60° C. for 1 hour the resulting mixture was stirred at 60° C. for 3 hours Acetonitrile was removed by azeotropic distillation The remaining mixture was washed with dichloromethane subjected to liquid separation When an aqueous solution of 25% sodium hydroxide was added to the water phase This crystal was filtered off under reduced pressure washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 40 ml of acetonitrile, 3.0 g (20.1 mmol) of trans-(-)-1,2-indandiol (I': trans-configuration: 98.0%; cis-configuration: 2.0%; optical purity: 100% e.e.) was dissolved. At room temperature, 3.2 g (31.7 mol) of 97% sulfuric acid was dropwise added thereto in a period of 30 minutes. After the resulting mixture was stirred at room temperature for 1 hour, the compound (I') disappeared from an HPLC. To the reaction liquid, 20 ml of water was added. Immediately thereafter, the mixture was heated and 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure. Then, the mixture was subjected to a reflux for 1.5 hours to complete the reaction. The reaction liquid was cooled to room temperature and washed twice with 10 ml of dichloromethane. Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide. The grayish white scaly crystal deposited thereby was filtered off under reduced pressure, washed with a small quantity of water, and then dried under reduced pressure to yield 1.77 g of cis-(-)-1-aminoindan-2-ol (V) as a primary crystal. Then, the mother liquid after the deposition of the crystal was extracted with dichloromethane and the extracted phase was concentrated to yield 0.69 g of the compound (V) as a secondary crystal. optical purity: 100% e.e.) was dissolved was added Immediately thereafter, the mixture was heated 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure a reflux for 1.5 hours the reaction The reaction liquid was cooled to room temperature washed twice with 10 ml of dichloromethane Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide The grayish white scaly crystal deposited thereby was filtered off under reduced pressure washed with a small quantity of water dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 100 ml four-neck flask, 4.48 g (30.3 mmol) of trans-(±)-1,2-indandiol (II) and 40 ml of acetonitrile were introduced. This mixture was suspended. While this suspension was stirred at room temperature, 6.14 g (60.6 mmol) of 97% sulfuric acid was added thereto at room temperature in a period of 20 minutes. The temperature within the mixture increased from 19° C. to 35° C. The slurry was completely dissolved to form a slightly yellow transparent solution. The solution was stirred at 24° C. for 1 hour and then at 60° C. for 1 hour. An HPLC analysis of the contents revealed that 70.8% of cis-oxazoline derivative (IV: R=CH3) had been generated, while no trans-amide derivative (III': R=CH3, Y=OH) was detected. Then, 30 ml of water was added thereto and the resulting mixture was stirred at 60° C. for 3 hours. Acetonitrile was removed by azeotropic distillation. The remaining mixture was washed with dichloromethane and then subjected to liquid separation. When an aqueous solution of 25% sodium hydroxide was added to the water phase, a crystal deposited. This crystal was filtered off under reduced pressure, washed with water, and then dried to yield 2.70 g (yield: 59.7%) of cis-(±)-1-aminoindan-2-ol (V) as a white crystal. Its purity determined by an HPLC was 97.7%. The temperature within the mixture increased from 19° C. to 35° C The slurry was completely dissolved to form a slightly yellow transparent solution The solution was stirred at 24° C. for 1 hour at 60° C. for 1 hour the resulting mixture was stirred at 60° C. for 3 hours Acetonitrile was removed by azeotropic distillation The remaining mixture was washed with dichloromethane subjected to liquid separation When an aqueous solution of 25% sodium hydroxide was added to the water phase This crystal was filtered off under reduced pressure washed with water dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C., and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1-amino-2-indanol (1.02 g, 63% yield). The mixture was gradually warmed to 20° C. and aged to 3 hours the mixture heated to reflux The resulting solid was removed by filtration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 40 ml of acetonitrile, 3.0 g (20.1 mmol) of trans-(-)-1,2-indandiol (I': trans-configuration: 98.0%; cis-configuration: 2.0%; optical purity: 100% e.e.) was dissolved. At room temperature, 3.2 g (31.7 mmol) of 97% sulfuric acid was dropwise added thereto in a period of 30 minutes. After the resulting mixture was stirred at room temperature for 1 hour, the compound (I') disappeared from an HPLC. To the reaction liquid, 20 ml of water was added. Immediately thereafter, the mixture was heated and 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure. Then, the mixture was subjected to a reflux for 1.5 hours to complete the reaction. The reaction liquid was cooled to room temperature and washed twice with 10 ml of dichloromethane. Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide. The grayish white scaly crystal deposited thereby was filtered off under reduced pressure, washed with a small quantity of water, and then dried under reduced pressure to yield 1.77 g of cis-(-)-1-aminoindan-2-ol (V) as a primary crystal. Then, the mother liquid after the deposition of the crystal was extracted with dichloromethane and the extracted phase was concentrated to yield 0.69 g of the compound (V) as a secondary crystal. optical purity: 100% e.e.) was dissolved was added Immediately thereafter, the mixture was heated 42 ml of an acetonitrile/water azeotrope was distilled off under normal pressure a reflux for 1.5 hours the reaction The reaction liquid was cooled to room temperature washed twice with 10 ml of dichloromethane Then, its pH was adjusted to 10.5 by an addition of an aqueous solution of 25% sodium hydroxide The grayish white scaly crystal deposited thereby was filtered off under reduced pressure washed with a small quantity of water dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 100 ml four-neck flask, 4.48 g (30.3 mmol) of trans-(±)-1,2-indandiol (I') and 40 ml of acetonitrile were introduced. This mixture was suspended. While this suspension was stirred at room temperature, 6.14 g (60.6 mmol) of 97% sulfuric acid was added thereto at room temperature in a period of 20 minutes. The temperature within the mixture increased from 19° C. to 35° C. The slurry was completely dissolved to form a slightly yellow transparent solution. The solution was stirred at 24° C. for 1 hour and then at 60° C. for 1 hour. An HPLC analysis of the contents revealed that 70.8% of cis-oxazoline derivative (IV: R=CH3) had been generated, while no trans-amide derivative (III': R=CH3, Y=OH) was detected. Then, 30 ml of water was added thereto and the resulting mixture was stirred at 60° C. for 3 hours. Acetonitrile was removed by azeotropic distillation. The remaining mixture was washed with dichloromethane and then subjected to liquid separation. When an aqueous solution of 25% sodium hydroxide was added to the water phase, a crystal deposited. This crystal was filtered off under reduced pressure, washed with water, and then dried to yield 2.70 g (yield: 59.7%) of cis-(±)-1-aminoindan-2-ol (V) as a white crystal. Its purity determined by an HPLC was 97.7%. The temperature within the mixture increased from 19° C. to 35° C The slurry was completely dissolved to form a slightly yellow transparent solution The solution was stirred at 24° C. for 1 hour at 60° C. for 1 hour the resulting mixture was stirred at 60° C. for 3 hours Acetonitrile was removed by azeotropic distillation The remaining mixture was washed with dichloromethane subjected to liquid separation When an aqueous solution of 25% sodium hydroxide was added to the water phase This crystal was filtered off under reduced pressure washed with water dried

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C. , and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1-amino-2-indanol (1.02 g, 63% yield). The mixture was gradually warmed to 20° C. and aged to 3 hours the mixture heated to reflux The resulting solid was removed by filtration

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C., and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1-amino-2-indanol (1.02 g, 63% yield). The mixture was gradually warmed to 20° C. and aged to 3 hours the mixture heated to reflux The resulting solid was removed by filtration