Diisopropylamine → HCID 12709724、化合物

温度

-20 °C

An LDA (14 mmol) solution was prepared by treating diisopropylamine (1.37 g, 14 mmol) with BuLi (1.6 M, 8.5 mL, 14 mmol) at −78° C. in dry THF (10 mL) under argon and allowing to warm up to −20° C. This solution was then cooled to −60° C. added to a solution of 1-benzyl-piperidine-4-ethyl carboxylate (3.05 g, 12 mmol) in THF (8 mL) at −60° C. and allowed to warm up to −40° C. over 1 h whereupon a solution of trans-beta-nitrostyrene (1.93 g, 13 mmol) in THF (8 mL) was added dropwise. The reaction mixture was allowed to warm up to room temperature over 1 h and then quenched with ammonium chloride (saturated, 40 mL) and the product extracted with ethyl acetate (2×40 mL). The combined organic extracts were then washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography on silica gel eluting with DCM:MeOH (9:1) afforded the title compound (4.1 g, 84%) as a light yellow gum. MS: m/e=397.4 (M+H).

1. temperatureThis solution was then cooled to −60° C.
2. additionwas added dropwise
3. temperatureto warm up to room temperature over 1 h
4. customquenched with ammonium chloride (saturated, 40 mL)
5. extractionthe product extracted with ethyl acetate (2×40 mL)
6. washThe combined organic extracts were then washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customevaporated
10. customPurification by chromatography on silica gel eluting with DCM:MeOH (9:1)

ORDレコード

ord-4cfcaf5e49ec43b695507a737ecaa876

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07173133B2