(Trimethylsilyl)acetonitrile → (Z)-1-(t-Butoxycarbonyl)-4-(t-butyldimethylsilyloxy)-3-(cyanomethylidene)piperidine

温度

-78 °C

To a solution of trimethylsilylacetonitrile (1.3 ml) in tetrahydrofuran (THF) (30 ml) was added at −78° C. lithium diisopropylamide (2.0 M in hexane, 4.7 ml). The resulting mixture was stirred at −78° C. for 0.5 hours, and then a solution of 1-(t-butoxycarbonyl)-4-(t-butyldimethylsilyloxy)piperidin-3-one (3 g) in THF (10 ml) was added at the same temperature. The resulting mixture was stirred for one hour while the temperature was raised to room temperature. The mixture was concentrated in vacuo, and the residue was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate (9:1) as the eluent to afford the title compound (880 mg, yield: 27%) as the less polar isomer as a yellow oil.

1. stirringThe resulting mixture was stirred for one hour while the temperature
2. temperaturewas raised to room temperature
3. concentrationThe mixture was concentrated in vacuo
4. customthe residue was purified by chromatography on silica gel using
5. additiona mixture of hexane and ethyl acetate (9:1) as the eluent

ORDレコード

ord-1dc922227a074c8992803e6e194ea0f5

出典データセット

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07829580B2