Hydrochloric Acid → HCID 20699034, compound

Participants

Reaction Steps

To a solution of 1.3 g (3.6 mmol) of N-Boc-4-(t-butyldimethylsilyloxy)proline methyl ester, prepared as described by Rosen et al., J. Med. Chem. 1988, 31, 1598, in 10 ml of methanol was added 5 ml (5 mmol) of 1 N LiOH in an ice bath. The reaction mixture was stirred for 30 min. The reaction mixture was adjusted to pH 2-3 with 1 N HCl at the same temperature and the solvent was evaporated. The resulting residue was partitioned between dichloromethane and water, and extracted 3 times with dichloromethane. The combined organic solution was washed with 1 N HCl and water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 1.05 g (96%) of N-Boc-4-(t-butyldimethylsilyl-oxy)proline as a foamy solid which was used without further purification.

Provenance & Evidence