Borane → tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution consisting of 3-carboxymethyl-azetidine-1-carboxylic acid tert-butyl ester (10.0 g, 46.5 mmol) and THF (15 mL) was cooled to 0° C. and treated with a 1 M solution of borane in THF (70 mL, 70 mmol), then slowly warmed to rt. After stirring for 18 h, the reaction mixture was quenched with 2 N NaOH (100 mL), diluted with H2O (100 mL), and extracted with Et2O (3×200 mL). The organic layers were combined, dried (MgSO4), and concentrated to give the title compound as a colorless oil (9.03 g, 97%). MS (ESI+): calcd. for C10H19NO3, 201.14. m/z found, 224.2 (M+Na)+. 1H NMR (d6-DMSO): 4.37 (t, J=5.1 Hz, 1H), 3.95-3.79 (m, 2H), 3.53-3.43 (m, 2H), 3.37 (dd, J=11.5, 6.2 Hz, 2H), 2.62-2.52 (m, 1H), 1.66 (dd, J=13.8, 6.4 Hz, 2H), 1.39-1.33 (m, 9H).

Provenance & Evidence