tert-Butanol → 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid

Participants

Reaction Steps

0.9 g of IV prepared in experiment (c) was refluxed for 16 hours in t-butanol containing 0.5 g potassium. The reaction mixture was allowed to cool, the solvent was evaporated under reduced pressure and the residue was poured into 20 ml of water. Dilute (4 N) hydrochloric acid was added until the solution was acidic and then extracted thrice with methylene chloride. The water layer was then passed over a column filled with Dowex 50W-X8 ion-exchange resin. Eluting the resin with ammonium hydroxide then gave the cis isomer of 3-azabicyclo(3.1.0)hexane-2-carboxylic acid.

Provenance & Evidence