1-methylcyclopentan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: BF3.Et2O (934 mg, 6.23 mmol) was added drop-wise at 20° C. to a stirred solution of 1-methylcyclopentanol (520 mg, 5.19 mmol) and trimethylsilyl azide (716 mg, 6.23 mmol) in 6 mL of toluene. Then the solution was stirred at room temperature for 16 hours. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL), and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the solvent was evaporated at 35° C. under reduced pressure to give 1-azido-1-methylcyclopentane (720 mg) as a crude product. It was used directly in the next step without further purification. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL) dried over anhydrous sodium sulfate The drying agent was removed by filtration the solvent was evaporated at 35° C. under reduced pressure

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

Procedure: BF3.Et2O (934 mg, 6.23 mmol) was added drop-wise at 20° C. to a stirred solution of 1-methylcyclopentanol (520 mg, 5.19 mmol) and trimethylsilyl azide (716 mg, 6.23 mmol) in 6 mL of toluene. Then the solution was stirred at room temperature for 16 hours. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL), and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the solvent was evaporated at 35° C. under reduced pressure to give 1-azido-1-methylcyclopentane (720 mg) as a crude product. It was used directly in the next step without further purification. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL) dried over anhydrous sodium sulfate The drying agent was removed by filtration the solvent was evaporated at 35° C. under reduced pressure

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

Procedure: A 250 ml tri-neck round bottom flask was equipped and a 50 ml addition funnel and the flask was cooled <0 C. 30 g of 1-methylcyclopentanol (0.3 M, 1 EQ) was added to the flask. 70% H2SO4 solution was prepared and cooled in an ice bath. The H2SO4 (12.71 ml, 0.91 M, 3 EQ) was added drop wise over 15 minutes and the reaction mixture was stirred for ˜2.5 hours in order to allow all the 1-methylcyclopentanol to dissolve. With the reaction stirring, 8.11 ml of H2O2 35% (wt) (0.24 M, 0.8 EQ) was added drop wise over 15 minutes. The reaction was left stirring overnight. The reaction mixture was transferred to a separation funnel and extracted three times with 50 ml of pentane each time. Organic layers were collected and the aqueous was set aside. The organic layers were extracted 3 times with 50 ml of 1N NaOH each time to remove excess acid. The organic layer was collected, dried and concentrated. The residue was purified by chromatography on a silica column using pentane as the mobile phase. The product fractions were concentrated to yield 973 mg of di(1-methyl-cyclopentyl)peroxide as a colorless oil. 13C-NMR (CDCl3) δ 24.43, 24.75, 37.13, 89.23 A 250 ml tri-neck round bottom flask was equipped a 50 ml addition funnel the flask was cooled <0 C cooled in an ice bath to dissolve With the reaction stirring The reaction was left stirring overnight The reaction mixture was transferred to a separation funnel extracted three times with 50 ml of pentane each time Organic layers were collected The organic layers were extracted 3 times with 50 ml of 1N NaOH each time to remove excess acid The organic layer was collected dried concentrated The residue was purified by chromatography on a silica column The product fractions were concentrated

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

Procedure: A 250 ml tri-neck round bottom flask was equipped and a 50 ml addition funnel and the flask was cooled <0 C. 30 g of 1-methylcyclopentanol (0.3 M, 1 EQ) was added to the flask. 70% H2SO4 solution was prepared and cooled in an ice bath. The H2SO4 (12.71 ml, 0.91 M, 3 EQ) was added drop wise over 15 minutes and the reaction mixture was stirred for ˜2.5 hours in order to allow all the 1-methylcyclopentanol to dissolve. With the reaction stirring, 8.11 ml of H2O2 35% (wt) (0.24 M, 0.8 EQ) was added drop wise over 15 minutes. The reaction was left stirring overnight. The reaction mixture was transferred to a separation funnel and extracted three times with 50 ml of pentane each time. Organic layers were collected and the aqueous was set aside. The organic layers were extracted 3 times with 50 ml of 1N NaOH each time to remove excess acid. The organic layer was collected, dried and concentrated. The residue was purified by chromatography on a silica column using pentane as the mobile phase. The product fractions were concentrated to yield 973 mg of di(1-methyl-cyclopentyl)peroxide as a colorless oil. 13C-NMR (CDCl3) δ 24.43, 24.75, 37.13, 89.23 A 250 ml tri-neck round bottom flask was equipped a 50 ml addition funnel the flask was cooled <0 C cooled in an ice bath to dissolve With the reaction stirring The reaction was left stirring overnight The reaction mixture was transferred to a separation funnel extracted three times with 50 ml of pentane each time Organic layers were collected The organic layers were extracted 3 times with 50 ml of 1N NaOH each time to remove excess acid The organic layer was collected dried concentrated The residue was purified by chromatography on a silica column The product fractions were concentrated

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

Procedure: Using the procedure of Step A of Example 15, 3 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-carboxyethynyl]-cyclopropane-carboxylate and 3 g of 1-methylcyclopentanol were reacted. The residue was chromatographed over silica gel and was eluted with an 8-2 n-hexane-ethyl acetate mixture to obtain 2 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[2-(1-methylcyclopentyloxycarbonyl)ethynyl]-cyclopropane-carboxylate. were reacted The residue was chromatographed over silica gel was eluted with an 8-2 n-hexane-ethyl acetate mixture

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

Procedure: BF3.Et2O (934 mg, 6.23 mmol) was added drop-wise at 20° C. to a stirred solution of 1-methylcyclopentanol (520 mg, 5.19 mmol) and trimethylsilyl azide (716 mg, 6.23 mmol) in 6 mL of toluene. Then the solution was stirred at room temperature for 16 hours. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL), and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the solvent was evaporated at 35° C. under reduced pressure to give 1-azido-1-methylcyclopentane (720 mg) as a crude product. It was used directly in the next step without further purification. The organic phase was washed with a 10% solution of NaHCO3 (10 mL), water (5 mL) and brine (5 mL) dried over anhydrous sodium sulfate The drying agent was removed by filtration the solvent was evaporated at 35° C. under reduced pressure

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

Procedure: A 250 ml tri-neck round bottom flask was equipped and a 50 ml addition funnel and the flask was cooled <0 C. 30 g of 1-methylcyclopentanol (0.3 M, 1 EQ) was added to the flask. 70% H2SO4 solution was prepared and cooled in an ice bath. The H2SO4 (12.71 ml, 0.91 M, 3 EQ) was added drop wise over 15 minutes and the reaction mixture was stirred for ˜2.5 hours in order to allow all the 1-methylcyclopentanol to dissolve. With the reaction stirring, 8.11 ml of H2O2 35% (wt) (0.24 M, 0.8 EQ) was added drop wise over 15 minutes. The reaction was left stirring overnight. The reaction mixture was transferred to a separation funnel and extracted three times with 50 ml of pentane each time. Organic layers were collected and the aqueous was set aside. The organic layers were extracted 3 times with 50 ml of 1N NaOH each time to remove excess acid. The organic layer was collected, dried and concentrated. The residue was purified by chromatography on a silica column using pentane as the mobile phase. The product fractions were concentrated to yield 973 mg of di(1-methyl-cyclopentyl)peroxide as a colorless oil. 13C-NMR (CDCl3) δ 24.43, 24.75, 37.13, 89.23 A 250 ml tri-neck round bottom flask was equipped a 50 ml addition funnel the flask was cooled <0 C cooled in an ice bath to dissolve With the reaction stirring The reaction was left stirring overnight The reaction mixture was transferred to a separation funnel extracted three times with 50 ml of pentane each time Organic layers were collected The organic layers were extracted 3 times with 50 ml of 1N NaOH each time to remove excess acid The organic layer was collected dried concentrated The residue was purified by chromatography on a silica column The product fractions were concentrated

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

Procedure: Using the procedure of Step A of Example 15, 3 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-carboxyethynyl]-cyclopropane-carboxylate and 3 g of 1-methylcyclopentanol were reacted. The residue was chromatographed over silica gel and was eluted with an 8-2 n-hexane-ethyl acetate mixture to obtain 2 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[2-(1-methylcyclopentyloxycarbonyl)-ethynyl]-cyclopropane-carboxylate. were reacted The residue was chromatographed over silica gel was eluted with an 8-2 n-hexane-ethyl acetate mixture

Conditions: temp:0.00; pressure:0.00; stir: