(Triphenylphosphoranylidene)acetonitrile → ((R)-3-cyano-1-methyl-allyl)-carbamic acid tert-butyl ester

HRID 246215

반응식

HRID 246215 반응식
[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].C1(P(=[CH:32][C:33]#[N:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:12])[NH:7][C@H:8]([CH3:11])[CH:9]=[CH:32][C:33]#[N:34])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

생성물 1

HCID 86677956((R)-3-cyano-1-methyl-allyl)-carbamic acid tert-butyl ester수율 63.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 20 mL scintillation vial, ((R)-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (2.5 g, 14.4 mmol) and (triphenylphosphoranylidene)acetonitrile (6.52 g, 21.7 mmol) were mixed in dichloromethane (20 mL) and stirred at room temperature for 16 h. The solvent was evaporated to give the crude material, which was purified by column chromatography (silica gel, gradient n-hexanes ethyl acetate) to provide 1.8 g (63%) of ((R)-3-cyano-1-methyl-allyl)-carbamic acid tert-butyl ester in a 3:1 diastereoselectivity (E:Z) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 6.38-6.79 (m, 1H), 5.47 (dd, J=16.24, 1.89 Hz, 1H), 4.48 (bs, 1H), 4.47 (bs, 1H), 1.45 (s, 1H), 1.28 (d, J=7.18 Hz, 9H).

후처리

  1. customThe solvent was evaporated
  2. customto give the crude material, which
  3. customwas purified by column chromatography (silica gel, gradient n-hexanes ethyl acetate)

출처 및 근거

ORD 기록
ord-fc346cea310b4a4e9983a907bd66bedf
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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