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

HRID 1917360
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HRID 1917360 반응식
[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[CH2:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24](Br)[CH:25]=[CH2:26].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[CH2:23])[C@H:12]([CH2:26][CH:25]=[CH2:24])[C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 67490859(3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 67490978(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester수율 50.6%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매2회

실험 절차

(3R)-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester (236.0 mg, 0.75 mmol) and allyl bromide (271.6 mg, 2.24 mmol) were dissolved in tetrahydrofuran. A 1 M solution of lithium hexamethyldisilazide in tetrahydrofuran (1.12 mL, 1.12 mmol) was added dropwise in a nitrogen atmosphere at 0° C. After stirring for 1.5 hours, a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 135 mg of the title compound as a colorless oil.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-33243f2c2711457597a11d4f4ba6eb54
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618094B2

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