Methanol → tert-Butyl N-(3-oxopropyl)carbamate

Participants

Reaction Steps

To a solution of 3-(t-butyloxycarbonylamino)propanol (1.419 g, 8.1 mmol) dissolved in DMSO (15 mL), IBX (2 eq, 4.5 g, 16.2 mmol) was added to form a slurry. The reaction was allowed to stir at rt for 5 hr. The solid IBX dissolved slowly, but a white precipitate formed after approximately 1 hr of reaction time. Distilled water (80 mL) was added to the reaction mixture, and the resultant aqueous solution filtered and then extracted with diethyl ether (3×175 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated. The crude oil was purified by silica gel chromatography using 10% CH3OH in CH2Cl2 as the eluent. The solvent was evaporated to leave a clear, colorless oil with a very pleasant flowery or candy-like scent: yield 67%; one spot on TLC, Rf=0.70 (10% CH3OH in CH2Cl2). 1H NMR (CDCl3) δ 9.80 (s, 1H), 4.94 (s, 1H), 3.47-3.38 (m, 2H), 2.27-2.65 (t, 2H), 1.47 (s, 9H). MS (ESI+) m/z 174 (M+1).

Provenance & Evidence