(1r,4r)-4-Hydroxycyclohexanecarbonitrile

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

Procedure: 6.4 g (51.1 mmol) of 4-hydroxy-cyclohexanecarbonitrile (121) were dissolved in 120 mL of dichloromethane, cooled to 0° C. and 14.9 mL (13.7 g, 128 mmol) of 2,6-lutidine and 15.4 mL (14.9 g, 56.2 mmol) of tert-butyldimethylsilyltrifluoromethanesulfonate were added. The reaction mixture was stirred for 16 h at room temperature, then additional 5.0 mL of tert-butyldimethylsilyltrifluoromethanesulfonate were added and stirring continued for 1 h. The reaction mixture was diluted with 100 mL of dichloromethane and washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine. The organic phase was dried over magnesium sulphate, filtered, concentrated in vacuo and purified by silica gel chromatography (heptanes:ethyl acetate) to give 9.76 g of the desired product. Rt=0.95 min (Method 18). Detected mass: 240.1 (M+H+). stirring continued for 1 h washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine The organic phase was dried over magnesium sulphate filtered concentrated in vacuo purified by silica gel chromatography (heptanes:ethyl acetate)

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

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane

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

Procedure: 6.4 g (51.1 mmol) of 4-hydroxy-cyclohexanecarbonitrile (121) were dissolved in 120 mL of dichloromethane, cooled to 0° C. and 14.9 mL (13.7 g, 128 mmol) of 2,6-lutidine and 15.4 mL (14.9 g, 56.2 mmol) of tert-butyldimethylsilyltrifluoromethanesulfonate were added. The reaction mixture was stirred for 16 h at room temperature, then additional 5.0 mL of tert-butyldimethylsilyltrifluoromethanesulfonate were added and stirring continued for 1 h. The reaction mixture was diluted with 100 mL of dichloromethane and washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine. The organic phase was dried over magnesium sulphate, filtered, concentrated in vacuo and purified by silica gel chromatography (heptanes:ethyl acetate) to give 9.76 g of the desired product. Rt=0.95 min (Method 18). Detected mass: 240.1 (M+H+). stirring continued for 1 h washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine The organic phase was dried over magnesium sulphate filtered concentrated in vacuo purified by silica gel chromatography (heptanes:ethyl acetate)

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

Procedure: 6.4 g (51.1 mmol) of 4-hydroxy-cyclohexanecarbonitrile (121) were dissolved in 120 mL of dichloromethane, cooled to 0° C. and 14.9 mL (13.7 g, 128 mmol) of 2,6-lutidine and 15.4 mL (14.9 g, 56.2 mmol) of tert-butyldimethylsilyltrifluoromethanesulfonate were added. The reaction mixture was stirred for 16 h at room temperature, then additional 5.0 mL of tert-butyldimethylsilyltrifluoromethanesulfonate were added and stirring continued for 1 h. The reaction mixture was diluted with 100 mL of dichloromethane and washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine. The organic phase was dried over magnesium sulphate, filtered, concentrated in vacuo and purified by silica gel chromatography (heptanes:ethyl acetate) to give 9.76 g of the desired product. Rt=0.95 min (Method 18). Detected mass: 240.1 (M+H+). stirring continued for 1 h washed with 100 mL of water, 80 mL of saturated aqueous sodium bicarbonate solution and 50 mL of brine The organic phase was dried over magnesium sulphate filtered concentrated in vacuo purified by silica gel chromatography (heptanes:ethyl acetate)

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

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane

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

Procedure: To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil. The product is extracted with a hexane-ether (1:1) mixture The organic phase is washed with a N HCl solution with water saturated with NaCl, before drying concentration The residue is purified by chromatography on a column of silica in dichloromethane