Formaldehyde → HCID 57667117, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (S)-2,2-dimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester (500 mg; example 2.a) at r.t. in methanol (10 ml) under an argon atmosphere were added formaldehyde (37% solution in H2O; 0.62 ml), zinc chloride (890 mg) and NaBH3CN (308 mg). The mixture was heated to 40° C. and stirring at that temperature was continued for 2 h. The mixture was concentrated and the residue was taken up in EtOAc/H2O. The biphasic mixture was filtered. The aqueous layer from the filtrate was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient:cyclohexane->cyclohexane/EtOAc 85:15) to give (S)-2,2-dimethyl-4-[(methyl-phenyl-amino)-methyl]-oxazolidine-3-carboxylic acid tert-butyl ester (462 mg, 88%) as colorless viscous oil. MS (ISP): 321.4 ([M+H]+)

Provenance & Evidence