Diethyl Ether → HCID 10725638, compound

Participants

Reaction Steps

Triethylamine (7.40 mL, 53.1 mmol) was added slowly to a mixture of (2S,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride (3.0 g, 17.7 mmol) in dichloromethane (41 mL) at 0° C. The mixture was stirred for 15 minutes. A mixture of triphosgene (1.79 g, 6.01 mmol) in dichloromethane (15 mL) was added drop wise via addition funnel. The mixture was allowed to warm to room temperature for 14 hours. Diethyl ether (20 mL) was added, and the mixture was cooled to −78° C. for 15 minutes. The solids were filtered and the filtrate was concentrated under reduced pressure to about 10 mL. The mixture was then added to a plug of silica gel and washed slowly with ethyl acetate (˜75 mL). The filtrate was then concentrated under reduced pressure and dried under vacuum to afford (4S,5R)-methyl 5-methyl-2-oxooxazolidine-4-carboxylate. 1H NMR (500 MHz, CDCl3) δ 5.96 (s, 1H), 4.77-4.71 (m, 1H), 3.99 (d, J=5.4 Hz, 1H), 3.81 (s, 3H), 1.56 (d, J=6.3 Hz, 3H).

Provenance & Evidence