Methanol → 3beta-Ornithyl-cholesterol-dihydrochloride

Participants

Reaction Steps

997 mg (3 mmol) of di-BOC-ornithine was dissolved in 40 ml of dichloromethane. 1.16 g (3 mmol) of cholesterol, 640 mg (3.1 mmol) of DCC, and 50 mg of DMAP were added, and the mixture was stirred at room temperature for 24 h. The dicyclohexylurea precipitate was removed by filtration, the solvent removed in vacuo and the residual solid was recrystallized from 5 ml of hexane yielding 1.62 g (77%) of 3β-di-BOC-ornithyl-cholesterol as a colorless, crystalline solid. 190 mg (0.27 mmol) of 3β-di-BOC-ornithyl-cholesterol was treated with 6 ml of MeOH (10 mmol HCl) and was stirred at ambient temperature for 1 h. Subsequent removal of the solvent under high vacuum yielded 146 mg (94%) of 3β-ornithyl-cholesterol-dihydrochloride VI as a colorless solid.

Provenance & Evidence