Hydrochloric Acid → 5,6,7,8-Tetrahydroindolizine-1-carboxylic acid

Participants

Reaction Steps

To a solution of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid ethyl ester (2b) (3.0 g, 15.5 mmol) in methanol (46 ml) was added water (23 ml) and potassium hydroxide (6.4 g, 97 mmol) and the mixture was stirred at reflux until complete conversion according to LC/MS (ca. 3 h). 160 ml water was added the mixture was acidified with excess hydrochloric acid. The forming precipitate was filtered off, washed once with water and dried in vacuo to give 2.02 g (79%) of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid as white solid. LC/MS (method 5; MS ionization method ES−): Rt=3.08 min; m/z=164.06 (M−H−).

Provenance & Evidence