Ethyl Acetate → HCID 86759215, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-benzyl-5-ethoxycarbonylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (30 g, 80 mol) in dry toluene (500 ml) was stirred at −78° C. during the addition of of 1M diisobutyl aluminium hydride in toluene (105 ml, 105 mmol). The resulting mixture was stirred at −78° C. for 4 hours and then ethyl acetate (60 ml) was added. After 30 minutes, the resulting mixture was allowed to warm to room temperature and a solution of potassium sodium L-tartrate tetrahydrate (90 g, mmol) in water (350 ml) was added. The resulting biphasic mixture was stirred until the two phases were clear. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (anhydrous magnesium sulfate) and concentrated in vacuo to provide 4-benzyl-2,2-dimethyl-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester which solidified upon standing overnight.

Provenance & Evidence