2-cyclohexylacetonitrile

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

Procedure: A solution of the cyclohexylacetic acid (20.0 g, 141 mmol) in CH2Cl2 (80 mL) was heated to reflux and a solution of chlorosulfonyl isocyanate (20.9 g, 148 mmol) in CH2Cl2 (18 mL) was added dropwise over 40 minutes. After the addition was complete, stirring was continued at reflux for 65 minutes. The mixture was cooled to 0° C., and DMF (21.1 g, 288 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred 18 hours. The mixture was poured over ice, the organic layer separated, and the aqueous layer extracted with CH2Cl2 (50 mL). The combined organic layers were washed with water (3×50 mL), brine, dried (Na2SO4), filtered through a plug of Florosil and concentrated. The nitrile was obtained as 14.6 g (85%) of an oil of sufficient purity for use in the next reaction. to reflux After the addition at reflux for 65 minutes to warm to room temperature stirred 18 hours The mixture was poured over ice the organic layer separated the aqueous layer extracted with CH2Cl2 (50 mL) The combined organic layers were washed with water (3×50 mL), brine dried (Na2SO4) filtered through a plug of Florosil concentrated

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

Procedure: A solution of sodium cyanide (2.77 g, 56.5 mmol) in 70 ml of DMF was treated with cyclohexyl bromide (7.9 ml, 56.5 mmol), under N2. The reaction mixture was reacted for 48 hours and then partitioned between EtOAc and H2O. The resultant layers were separated and the organic layer was concentrated in vacuo. The crude material was purified using flash chromatography (eluent of 5% EtOAc in hexanes). The reaction mixture was reacted for 48 hours partitioned between EtOAc and H2O The resultant layers were separated the organic layer was concentrated in vacuo The crude material was purified

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

Procedure: To a solution of 0.846 g (8.1 mmol) of hydroxylamine hydrochloride in 11 mL of isopropyl alcohol, 1.499 g (17.8 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25° C. to 30° C. for 10-15 min. 1.0 g (8.1 mmol) of 2-cyclohexylacetonitrile was added and stirred at 80° C. to 85° C. for 3-4 h. After completion of the reaction, the reaction mixture was cooled to 25° C. to 30° C., filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue was chased with 5 mL of toluene to yield the title compound. stirred at 80° C. to 85° C. for 3-4 h After completion of the reaction the reaction mixture was cooled to 25° C. to 30° C. filtered washed with 2 mL of isopropyl alcohol The filtrate was collected distilled out completely to obtain a crude residue

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

Procedure: A solution of the cyclohexylacetic acid (20.0 g, 141 mmol) in CH2Cl2 (80 mL) was heated to reflux and a solution of chlorosulfonyl isocyanate (20.9 g, 148 mmol) in CH2Cl2 (18 mL) was added dropwise over 40 minutes. After the addition was complete, stirring was continued at reflux for 65 minutes. The mixture was cooled to 0° C., and DMF (21.1 g, 288 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred 18 hours. The mixture was poured over ice, the organic layer separated, and the aqueous layer extracted with CH2Cl2 (50 mL). The combined organic layers were washed with water (3×50 mL), brine, dried (Na2SO4), filtered through a plug of Florosil and concentrated. The nitrile was obtained as 14.6 g (85%) of an oil of sufficient purity for use in the next reaction. to reflux After the addition at reflux for 65 minutes to warm to room temperature stirred 18 hours The mixture was poured over ice the organic layer separated the aqueous layer extracted with CH2Cl2 (50 mL) The combined organic layers were washed with water (3×50 mL), brine dried (Na2SO4) filtered through a plug of Florosil concentrated

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

Procedure: A solution of the cyclohexylacetic acid (20.0 g, 141 mmol) in CH2Cl2 (80 mL) was heated to reflux and a solution of chlorosulfonyl isocyanate (20.9 g, 148 mmol) in CH2Cl2 (18 mL) was added dropwise over 40 minutes. After the addition was complete, stirring was continued at reflux for 65 minutes. The mixture was cooled to 0° C., and DMF (21.1 g, 288 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred 18 hours. The mixture was poured over ice, the organic layer separated, and the aqueous layer extracted with CH2Cl2 (50 mL). The combined organic layers were washed with water (3×50 mL), brine, dried (Na2SO4), filtered through a plug of Florosil and concentrated. The nitrile was obtained as 14.6 g (85%) of an oil of sufficient purity for use in the next reaction. to reflux After the addition at reflux for 65 minutes to warm to room temperature stirred 18 hours The mixture was poured over ice the organic layer separated the aqueous layer extracted with CH2Cl2 (50 mL) The combined organic layers were washed with water (3×50 mL), brine dried (Na2SO4) filtered through a plug of Florosil concentrated

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

Procedure: A solution of sodium cyanide (2.77 g, 56.5 mmol) in 70 ml of DMF was treated with cyclohexyl bromide (7.9 ml, 56.5 mmol), under N2. The reaction mixture was reacted for 48 hours and then partitioned between EtOAc and H2O. The resultant layers were separated and the organic layer was concentrated in vacuo. The crude material was purified using flash chromatography (eluent of 5% EtOAc in hexanes). The reaction mixture was reacted for 48 hours partitioned between EtOAc and H2O The resultant layers were separated the organic layer was concentrated in vacuo The crude material was purified

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

Procedure: To a solution of 0.846 g (8.1 mmol) of hydroxylamine hydrochloride in 11 mL of isopropyl alcohol, 1.499 g (17.8 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25° C. to 30° C. for 10-15 min. 1.0 g (8.1 mmol) of 2-cyclohexylacetonitrile was added and stirred at 80° C. to 85° C. for 3-4 h. After completion of the reaction, the reaction mixture was cooled to 25° C. to 30° C., filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue was chased with 5 mL of toluene to yield the title compound. stirred at 80° C. to 85° C. for 3-4 h After completion of the reaction the reaction mixture was cooled to 25° C. to 30° C. filtered washed with 2 mL of isopropyl alcohol The filtrate was collected distilled out completely to obtain a crude residue

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

Procedure: A solution of the cyclohexylacetic acid (20.0 g, 141 mmol) in CH2Cl2 (80 mL) was heated to reflux and a solution of chlorosulfonyl isocyanate (20.9 g, 148 mmol) in CH2Cl2 (18 mL) was added dropwise over 40 minutes. After the addition was complete, stirring was continued at reflux for 65 minutes. The mixture was cooled to 0° C., and DMF (21.1 g, 288 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred 18 hours. The mixture was poured over ice, the organic layer separated, and the aqueous layer extracted with CH2Cl2 (50 mL). The combined organic layers were washed with water (3×50 mL), brine, dried (Na2SO4), filtered through a plug of Florosil and concentrated. The nitrile was obtained as 14.6 g (85%) of an oil of sufficient purity for use in the next reaction. to reflux After the addition at reflux for 65 minutes to warm to room temperature stirred 18 hours The mixture was poured over ice the organic layer separated the aqueous layer extracted with CH2Cl2 (50 mL) The combined organic layers were washed with water (3×50 mL), brine dried (Na2SO4) filtered through a plug of Florosil concentrated