Sodium Carbonate → HCID 15430829, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 100 ml 3-necked round bottom flask was fitted with a reflux condenser, thermometer and magnetic stirrer and the apparatus filled with a nitrogen atmosphere. Phosphorous oxychloride (8.89 g, 58 mmol) and pyridine (44 ml) were charged and the mixture then cooled to −10° C. in an acetone/Drikold™ bath. 3-Cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane (6.17 g, 26.4 mmol—assumed) was added in one portion and the resulting exotherm raised the reaction mass temperature to 28° C. The mixture was then heated to 80° C. and held at this temperature overnight. The reaction mass was cooled to ambient (precipitation occurred) and added to a stirred mixture of saturated aqueous sodium carbonate (200 ml) and ethyl acetate (200 ml). The layers were separated and the aqueous then extracted with ethyl acetate (2×200 ml). The combined organics were washed with brine (100 ml), dried (Na2SO4) and concentrated in vacuo to give 3-cyano-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1 ]oct-2-ene (2.5 g, 35% yield).

Provenance & Evidence