Diisopropylethylamine → {4-[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-piperidin-1-yl}-carbamic acid t-butyl ester

温度

0 °C

4-[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-piperidine hydrochloride (1:1) (300 mg, 1.07 mmol) was combined with dichloromethane (15 mL) to give a light yellow suspension. N,N-Diisopropylethylamine (166 mg, 225 μl, 1.29 mmol) was added at 0° C. Subsequently 3-(4-cyanophenyl)-2-oxaziridinecarboxylic acid 1,1-dimethylethyl ester (238 mg, 965 μmol) in dichloromethane (10 mL) was added during 20 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 40% ethyl acetate in n-heptane) to deliver an oil contaminated with 4-cyano-benzaldehyde. This material was purified by a second chromatography (aminophase 10 g, ethyl acetetate/n-heptane 1/1) to give the title compound (0.23 g, 60%) as a white solid; LC-MS (ESI) 94.9%, 359.2710 (M+H)+.

1. customto give a light yellow suspension
2. concentrationAfterwards the reaction mixture was concentrated in vacuo
3. customthe residue was purified by flash chromatography (silica gel, 20 g, 0% to 40% ethyl acetate in n-heptane)
4. customThis material was purified by a second chromatography (aminophase 10 g, ethyl acetetate/n-heptane 1/1)

ORDレコード

ord-bf19fc577870467db2199ee4be9095f6

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08648099B2