Hydrochloric Acid → HCID 18316935, compound

Participants

Reaction Conditions

Reaction Steps

A 500 ml 3-necked round bottom flask was equipped with an overhead paddle stirrer, thermometer and hypochorite scrubber. 8-(2,2,2-Trifluoroethyl)-8-azabicyclo[3.2.1]octan-3-one (10.82 g, 50 mmol) was charged to the reaction flask followed by hydrochloric acid (5M, 100 ml) and the mixture was cooled to 0° C. Diethyl ether (70.8 g, 955 mmol) was added and the mixture stirred for 5 minutes. Potassium cyanide (36.9 g, 550 mmol) was added to the stirred reaction mixture portionwise over 0.5 hour. After complete addition the resultant pink mixture was stirred for 3 hour at about 3° C. The pH of the mixture was adjusted to 5.8 using hydrochloric acid (5M), water (50 ml) was added and the pH re-adjusted from 7 to 5.8. The organic layer was separated off and the aqueous phase was extracted with diethyl ether (2×100 ml). The ether extracts were combined, washed with highly dilute (pH 5.6) hydrochloric acid to leave a solution of 3-cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane in diethyl ether (303 ml).

Provenance & Evidence