Diisopropylethylamine → N'-[3-(t-Butyl-dimethyl-silanyloxy)-propyl]-N'-methyl-hydrazinecarboxylic acid t-butyl ester

Participants

Reaction Conditions

Reaction Steps

3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-N-methyl-1-propanamine hydrochloride (1:1) (720 mg, 3.0 mmol) was combined with dichloromethane (30 mL) to give a colorless solution. N,N-Diisopropylethylamine (313 mg, 423 μl, 2.42 mmol) was added at 0° C. Subsequently 3-(4-cyanophenyl)-2-oxaziridinecarboxylic acid 1,1-dimethylethyl ester (542 mg, 2.2 mmol) in dichloromethane (20 mL) was added during 15 min at 0° C. and the reaction mixture was stirred for 1 h at 0° C. Afterwards the reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 20 g, 0% to 70% ethyl acetate in n-heptane) to deliver an oil contaminated with 4-cyano-benzaldehyde. This material was purified by a second chromatography (aminophase 20 g, ethyl acetate/n-heptane 1/1) to give the title compound as colorless oil.

Provenance & Evidence