1-Boc-Azetidine-3-carboxylic acid → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a tetrahydrofuran (100 mL) solution of 1-(tert-butoxycarbonyl)-3-azetidinecarboxylic acid (2.0 g, 9.94 mmol), 10M-borane-dimethyl sulfide complex (2.98 mL, 29.8 mmol) was added at room temperature, and the mixture was stirred for 14 hours. The reaction liquor was poured onto ice water (100 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, 2% methanol/ethyl acetate), to obtain the title compound (1.83 g, 98%) as an oily matter.

Provenance & Evidence