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(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester → [(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester

HRID 1917361
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HRID 1917361 반응식
[C:1]([O:5][C:6]([C@@:8]1([CH:25]=C)[C@H:12]([CH2:13][CH:14]=C)[C:11](=[O:16])[N:10]([C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1C=CC=CC=1.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:1]([O:5][C:6]([C@@:8]12[CH:25]=[CH:14][CH2:13][C@@H:12]1[C:11](=[O:16])[N:10]([C@@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 67490978(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 67490826[(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester수율 76.9%

시약·촉매·용매 2

HCID 178425456HCID 178425456, 화합물촉매HCID 241Benzene용매

실험 절차

(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester (130.0 mg, 0.37 mmol) was dissolved in benzene (8 mL). The second generation Grubbs' catalyst (31.0 mg, 0.04 mmol) was added, and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (15% ethyl acetate/hexane) to give 93.2 mg of the title compound as a yellow oil.

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ef0ca84b1c4649b5ac186a4ba5809222
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618094B2

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