Hydrochloric Acid → (2S)-1-(Benzyloxycarbonyl)azetidine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-methyl-1-(benzyloxycarbonyl)azetidine-2-carboxylate (0.78 g, 3.12 mmol) in a 1:1 mixture of ether:methanol (25.0 mL) was added 1N LiOH in water (5.8 mL) at about 0° C. The mixture was stirred under argon at about 0° C. for about 30 minutes and then at about room temperature overnight. The pH was adjusted to about pH 1 by adding 1N HCl, then the mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give 0.78 g (99% yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 2.45-2.63 (br, 2H); 4.00 (t, 2H, J=7.7); 4.77-4.90 (br, 1H); 5.16 (s, 2H); 7.37 (s, 5H).

Provenance & Evidence