Hydrochloric Acid → HCID 18316935, compound

Participants

Reaction Conditions

Reaction Steps

A 50 ml 3-necked round bottom flask was equipped with a magnetic stirrer, thermometer and hypochiorite scrubber. 8-(2,2,2-Trifluoroethyl)-8-azabicyclo[3.2.1]octan-3-one (1.06 g, 5 mmol) was charged to the reaction flask followed by hydrochloric acid (5M, 10 ml) and the mixture was cooled to 0° C. Diethyl ether (7 g) was added and the mixture stirred for 5 minutes. Potassium cyanide (3.69 g, 55 mmol) was added portionwise to the stirred, cooled reaction mixture over 0.25 hour. After complete addition the resultant pink mixture was stirred for 3 hours at 5° C. Water (10 ml) was added, the organic layer separated and the aqueous phase extracted with diethyl ether (2×10 ml). The combined ether extracts were dried (Na2SO4), filtered and concentrated in vacuo (without heat) to give 3-cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane (1.13 g) as a dark red oil which solidified on standing and this was used directly in Step 2.

Provenance & Evidence