Ethanol → HCID 117840918, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 ml three-mouthed flask were charged crude (1S,2R)-ethyl 2-{4-(difluoromethoxy)benzoyl}aminocyclohexane-1-carboxylate (14 g, 41.0 mmol), and ethanol (42 ml), and the mixture was heated to 40° C. 5N Aqueous sodium hydroxide solution (9 ml, 45 mmol) was added, and the mixture was stirred at 40° C. for 2 hr 30 min. After cooling to 25° C., water (89 ml), toluene (28 ml) and heptane (28 ml) were added. The mixture was stirred and the aqueous layer was obtained. The aqueous layer was washed with a mixture of toluene (28 ml) and heptane (28 ml). To the aqueous layer was added acetonitrile (14 ml), and 6N hydrochloric acid and water (47 ml) were added to give crystals. The resulting crystals were collected by filtration, washed with water (70 ml) and then dried to give the title compound as a crude product. Recrystallization from an acetonitrile (80 ml)-water (120 ml) system gave the title compound as pale-gray crystals. yield 8.3 g. (diastereomeric excess>99.9% de) (enantiomeric excess>99.9% ee)

Provenance & Evidence