Aniline → (RS)-2,2,4-trimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (RS)-4-formyl-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (300 mg) at r.t. in methanol (3 ml) was added aniline (132 mg) and the mixture was heated at 80° C. for 3 h. NaBH4 (93 mg) was then added and the mixture was stirred at 60° C. for 16 h, then cooled to r.t. and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient:heptane/ethyl acetate) to give (RS)-2,2,4-trimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester (181 mg, 46%) as a yellow oil. MS (ISP): 321.1 ([M+H]+).

Provenance & Evidence