cyclohexylmethyl methanesulfonate

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

Procedure: To 465 g (4.3 moles) of 2-(aminomethyl) pyridine was added with stirring 456 g (4.3 moles) of benzaldehyde. The temperature was increased to 70°-80° C. The mixture was diluted with 2 L of MTBE and the water was removed by stirring the solution with 200 g of sodium sulfate overnight. The mixture was filtered and washed with 2 L of MTBE. To remove the remaining water, 100 g of molecular sieves were added. To the mixture was added 483 g (4.3 moles) potassium t-butoxide in portions followed by 842 g (4.38 moles) of cyclohexylmethyl methanesulfonate. After 10-20 hours, the mixture was hydrolyzed by the addition of 5 L water containing 720 mL of hydrochloric acid. The organic phase was separated and discarded. The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide. The product was extracted with petroleum ether to yield 452 g of crude mine. The amine was purified by vacuum distillation at 88° C. and 0.5 Torr to give 353 g (35%) of 1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine. The temperature was increased to 70°-80° C the water was removed The mixture was filtered washed with 2 L of MTBE To remove the remaining water, 100 g of molecular sieves were added After 10-20 hours The organic phase was separated The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide The product was extracted with petroleum ether to yield 452 g of crude mine The amine was purified by vacuum distillation at 88° C.

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

Procedure: Cyclohexylmethanol (1.25 mL, 10.0 mmol) was dissolved in CH2Cl2 (50 mL), treated with diisopropylethylamine (7.0 mL, 40.0 mmol), cooled to 0° C., treated with methanesulfonyl chloride (0.85 mL, 11.0 mmol), and stirred for 1 hour at room temperature. The reaction was diluted with CH2Cl2 (200 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 2.42 g (125% crude yield) of the desired product which was used immediately without purification. washed with saturated bicarbonate solution and brine dried over Na2SO4 concentrated

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

Procedure: To 465 g (4.3 moles) of 2-(aminomethyl) pyridine was added with stirring 456 g (4.3 moles) of benzaldehyde. The temperature was increased to 70°-80° C. The mixture was diluted with 2 L of MTBE and the water was removed by stirring the solution with 200 g of sodium sulfate overnight. The mixture was filtered and washed with 2 L of MTBE. To remove the remaining water, 100 g of molecular sieves were added. To the mixture was added 483 g (4.3 moles) potassium t-butoxide in portions followed by 842 g (4.38 moles) of cyclohexylmethyl methanesulfonate. After 10-20 hours, the mixture was hydrolyzed by the addition of 5 L water containing 720 mL of hydrochloric acid. The organic phase was separated and discarded. The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide. The product was extracted with petroleum ether to yield 452 g of crude mine. The amine was purified by vacuum distillation at 88° C. and 0.5 Torr to give 353 g (35%) of 1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine. The temperature was increased to 70°-80° C the water was removed The mixture was filtered washed with 2 L of MTBE To remove the remaining water, 100 g of molecular sieves were added After 10-20 hours The organic phase was separated The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide The product was extracted with petroleum ether to yield 452 g of crude mine The amine was purified by vacuum distillation at 88° C.

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

Procedure: To 465 g (4.3 moles) of 2-(aminomethyl) pyridine was added with stirring 456 g (4.3 moles) of benzaldehyde. The temperature was increased to 70°-80° C. The mixture was diluted with 2 L of MTBE and the water was removed by stirring the solution with 200 g of sodium sulfate overnight. The mixture was filtered and washed with 2 L of MTBE. To remove the remaining water, 100 g of molecular sieves were added. To the mixture was added 483 g (4.3 moles) potassium t-butoxide in portions followed by 842 g (4.38 moles) of cyclohexylmethyl methanesulfonate. After 10-20 hours, the mixture was hydrolyzed by the addition of 5 L water containing 720 mL of hydrochloric acid. The organic phase was separated and discarded. The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide. The product was extracted with petroleum ether to yield 452 g of crude mine. The amine was purified by vacuum distillation at 88° C. and 0.5 Torr to give 353 g (35%) of 1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine. The temperature was increased to 70°-80° C the water was removed The mixture was filtered washed with 2 L of MTBE To remove the remaining water, 100 g of molecular sieves were added After 10-20 hours The organic phase was separated The aqueous phase was washed with 0.5 L of methylene chloride and basified with 0.5 L of ammonium hydroxide The product was extracted with petroleum ether to yield 452 g of crude mine The amine was purified by vacuum distillation at 88° C.

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

Procedure: Cyclohexylmethanol (1.25 mL, 10.0 mmol) was dissolved in CH2Cl2 (50 mL), treated with diisopropylethylamine (7.0 mL, 40.0 mmol), cooled to 0° C., treated with methanesulfonyl chloride (0.85 mL, 11.0 mmol), and stirred for 1 hour at room temperature. The reaction was diluted with CH2Cl2 (200 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 2.42 g (125% crude yield) of the desired product which was used immediately without purification. washed with saturated bicarbonate solution and brine dried over Na2SO4 concentrated