Boc-(+/-)-trans-2-aminocyclohexanol

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

Procedure: 3.51 g racemic trans-(2-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester were added to a suspension of 3.09 g lithium aluminium hydride in THF. The reaction mixture was heated at reflux over night. After that time subsequently 3.1 ml water, 3.1 ml sodium hydroxide solution (2M) and 3.1 ml water were added. The mixture was then stirred for 45 minutes and then filtered through celite. The celite was washed with EtOAc. The solvent was evaporated. The reaction mixture was heated at reflux over night filtered through celite The celite was washed with EtOAc The solvent was evaporated

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

Procedure: A solution of 3.0 g of (1R,2R)-N-tert-butoxycarbonyl-2-benzyloxycyclohexylamine in 100 mL of methanol was combined with 300 mg of 5% palladium on carbon, and hydrogenated at room temperature under atmospheric pressure. After 48 hours, palladium on carbon was filtered off, and the filtrate was concentrated. The residue was subjected to chromatography on silica gel (n-hexane:ethyl acetate 2:1) to obtain 2.0 g of the desirable compound. hydrogenated at room temperature palladium on carbon was filtered off the filtrate was concentrated

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

Procedure: A solution of 3.0 g of (1R,2R)-N-tert-butoxycarbonyl-2-benzyloxycyclohexylamine in 100 mL of methanol was combined with 300 mg of 5% palladium on carbon, and hydrogenated at room temperature under atmospheric pressure. After 48 hours, palladium on carbon was filtered off, and the filtrate was concentrated. The residue was subjected to chromatography on silica gel (n-hexane:ethyl acetate 2:1) to obtain 2.0 g of the desirable compound. hydrogenated at room temperature palladium on carbon was filtered off the filtrate was concentrated

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

Procedure: To a stirred slurry of trans-tert-butyl 2-hydroxycyclohexylcarbamate (1.00 g, 4.64 mmol), PPh3 (1.34 g, 5.10 mmol) and phthalimide (1.50 g, 10.20 mmol) in a 2:1 mixture of toluene and THF (15 mL) was added diisopropyl azodicarboxylate (1.0 mL, 5.10 mmol) dropwise over a period of 1 h. Once the addition was complete, the mixture was stirred at about 0° C. for 7 h and was then warmed slowly to 7° C. over a period of 14 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (3.90 g). The crude product was used in the next step without further purification. Once the addition was then warmed slowly to 7° C. over a period of 14 h The mixture was filtered the filtrate was concentrated under reduced pressure

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

Procedure: To a stirred slurry of trans-tert-butyl 2-hydroxycyclohexylcarbamate (1.00 g, 4.64 mmol), PPh3 (1.34 g, 5.10 mmol) and phthalimide (1.50 g, 10.20 mmol) in a 2:1 mixture of toluene and THF (15 mL) was added diisopropyl azodicarboxylate (1.0 mL, 5.10 mmol) dropwise over a period of 1 h. Once the addition was complete, the mixture was stirred at about 0° C. for 7 h and was then warmed slowly to 7° C. over a period of 14 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (3.90 g). The crude product was used in the next step without further purification. Once the addition was then warmed slowly to 7° C. over a period of 14 h The mixture was filtered the filtrate was concentrated under reduced pressure

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

Procedure: 3.51 g racemic trans-(2-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester were added to a suspension of 3.09 g lithium aluminium hydride in THF. The reaction mixture was heated at reflux over night. After that time subsequently 3.1 ml water, 3.1 ml sodium hydroxide solution (2M) and 3.1 ml water were added. The mixture was then stirred for 45 minutes and then filtered through celite. The celite was washed with EtOAc. The solvent was evaporated. The reaction mixture was heated at reflux over night filtered through celite The celite was washed with EtOAc The solvent was evaporated

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

Procedure: To a solution of (1R,2R) (2-benzyloxycyclohexyl) carbamic acid tert-butyl ester (7 g, 23 mmoles) in a 9:1 mixture of ethyl acetate and methanol (80 mL), 10% Pd—C (1.13 g) was added and hydrogenated at 35 psi for 4 h. The catalyst was removed by filtration through a celite pad. The filtrate was concentrated to give the title compound as an oil (4.7 g, 95%). MS: (M+1): 215.95 was added The catalyst was removed by filtration through a celite pad The filtrate was concentrated

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

Procedure: To a solution of (1R,2R) (2-benzyloxycyclohexyl) carbamic acid tert-butyl ester (7 g, 23 mmoles) in a 9:1 mixture of ethyl acetate and methanol (80 mL), 10% Pd—C (1.13 g) was added and hydrogenated at 35 psi for 4 h. The catalyst was removed by filtration through a celite pad. The filtrate was concentrated to give the title compound as an oil (4.7 g, 95%). MS: (M+1): 215.95 was added The catalyst was removed by filtration through a celite pad The filtrate was concentrated

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

Procedure: To a stirred slurry of trans-tert-butyl 2-hydroxycyclohexylcarbamate (1.00 g, 4.64 mmol), PPh3 (1.34 g, 5.10 mmol) and phthalimide (1.50 g, 10.20 mmol) in a 2:1 mixture of toluene and THF (15 mL) was added diisopropyl azodicarboxylate (1.0 mL, 5.10 mmol) dropwise over a period of 1 h. Once the addition was complete, the mixture was stirred at about 0° C. for 7 h and was then warmed slowly to 7° C. over a period of 14 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (3.90 g). The crude product was used in the next step without further purification. Once the addition was then warmed slowly to 7° C. over a period of 14 h The mixture was filtered the filtrate was concentrated under reduced pressure

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

Procedure: A solution of 3.0 g of (1R,2R)-N-tert-butoxycarbonyl-2-benzyloxycyclohexylamine in 100 mL of methanol was combined with 300 mg of 5% palladium on carbon, and hydrogenated at room temperature under atmospheric pressure. After 48 hours, palladium on carbon was filtered off, and the filtrate was concentrated. The residue was subjected to chromatography on silica gel (n-hexane:ethyl acetate 2:1) to obtain 2.0 g of the desirable compound. hydrogenated at room temperature palladium on carbon was filtered off the filtrate was concentrated

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

Procedure: To a stirred slurry of trans-tert-butyl 2-hydroxycyclohexylcarbamate (1.00 g, 4.64 mmol), PPh3 (1.34 g, 5.10 mmol) and phthalimide (1.50 g, 10.20 mmol) in a 2:1 mixture of toluene and THF (15 mL) was added diisopropyl azodicarboxylate (1.0 mL, 5.10 mmol) dropwise over a period of 1 h. Once the addition was complete, the mixture was stirred at about 0° C. for 7 h and was then warmed slowly to 7° C. over a period of 14 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (3.90 g). The crude product was used in the next step without further purification. Once the addition was then warmed slowly to 7° C. over a period of 14 h The mixture was filtered the filtrate was concentrated under reduced pressure

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

Procedure: To a stirred slurry of trans-tert-butyl 2-hydroxycyclohexylcarbamate (1.00 g, 4.64 mmol), PPh3 (1.34 g, 5.10 mmol) and phthalimide (1.50 g, 10.20 mmol) in a 2:1 mixture of toluene and THF (15 mL) was added diisopropyl azodicarboxylate (1.0 mL, 5.10 mmol) dropwise over a period of 1 h. Once the addition was complete, the mixture was stirred at about 0° C. for 7 h and was then warmed slowly to 7° C. over a period of 14 h. The mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (3.90 g). The crude product was used in the next step without further purification. Once the addition was then warmed slowly to 7° C. over a period of 14 h The mixture was filtered the filtrate was concentrated under reduced pressure