(S)-Tert-butyl 2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate → (S)-4-(2-hydroxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

(S)-2,2-Dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid t-butyl ester (2.29 g, 9.44 mmol) was dissolved in dry tetrahydrofuran (25 mL). Then at −78° C., allyl magnesium bromide (1.0M in diethyl ether, 9.9 mL) was added. The mixture was warmed to −15° C. and stirred for 2 h. The mixture was extracted with diethyl ether and aqueous citric acid solution. The organic layer was washed with saturated sodium chloride solution, dried over sodium sulfate and solvents were evaporated to afford (S)-4-(2-hydroxy-pent-4-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.54 g) as an oil.

Provenance & Evidence