Methanol → HCID 15430828, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 10 ml round bottom flask was fitted with a reflux condenser and magnetic stirrer and the apparatus filled with a nitrogen atmosphere. 3-Cyano-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]oct-2-ene (0.216 g, 1 mmol) was charged to the flask followed by methanol (0.5 ml) and pyridine (1.5 ml) to give a solution. Sodium borohydride (0.046 g, 1.2 mmol) was added in a single portion and the mixture was heated to 80° C. The reaction was held at this temperature overnight, refluxed for 3 hours and then cooled to ambient. Saturated aqueous potassium dihydrogen phosphate (10 ml) was added to the reaction mass and the aqueous solution (pH7) was then extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo to give 3-cyano-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane (0.22 g, 74% yield) as a mixture of epimers (12:1 equatorial:axial).

Provenance & Evidence