Methanol, magnesium salt (2:1) → HCID 15430828, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 50 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 (0.26 g, 1 mmol) was charged to the reactor followed by methanol (10 ml). Magnesium turnings (1.0 g, 40 mmol) were added in a single portion and after an induction period of 0.25 hours, a vigorous reaction occurred which was moderated by cooling with an ice bath. The mixture was stirred at 0° C. for 1 hour, during which time the reaction mass thickened (due to magnesium methoxide formation), and was then allowed to warm to ambient. The reaction mixture was added to a solution of potassium dihydrogen phosphate (10 g) in water (40 ml) and stirred for 0.5 hour. Residual solid was removed by filtration and the aqueous filtrate was extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (Na2SO4) and concentrated in vacuo to give 3-cyano-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane (0.6 g, 72% yield) as a mixture of epimers (25:75 exo:endo).

Provenance & Evidence