Methanol → HCID 53952369, compound

Participants

Reaction Steps

An oven-dried 10 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer and placed under an atmosphere of nitrogen. 3-Cyano-8-(2,2-difluoroethyl)-8-azabicyclo[3.2.1]oct-2-ene (0.17 g, 0.53 mmol) was charged to the reactor followed by methanol (0.25 ml) and pyridine (0.75 ml) to give a solution. Solid sodium borohydride (0.039 g, 1.03 mmol) was added in a single portion and the mixture was then heated and held at reflux for 3 hour. After cooling to ambient, the reaction mass was poured into an agitated saturated aqueous potassium dihydrogen phosphate (10 ml) solution. The aqueous solution was extracted with dichloromethane (3×10 ml) and the combined organic layers were dried (Na2SO4). Concentration in vacuo to give 3-cyano-8-(2,2-difluoroethyl)-8-azabicyclo-[3.2.1]octane(0. 197 g, 95% yield) as a mixture of epimers (90:10 exo:endo).

Provenance & Evidence