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Hexane → (3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917359
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인쇄 미리보기

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HRID 1917359 반응식
[CH2:1]([Li])CCC.CCCCCC.[C:12]([O:16][C:17]([C@@:19]1([CH:33]=O)[CH2:23][C:22](=[O:24])[N:21]([C@@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:12]([O:16][C:17]([C@@:19]1([CH:33]=[CH2:1])[CH2:23][C:22](=[O:24])[N:21]([C@@H:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH3:26])[CH2:20]1)=[O:18])([CH3:14])([CH3:13])[CH3:15]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 86664650(3S)-3-Formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

생성물 1

HCID 67490859(3R)-5-Oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 74505
Methyltriphenyliphosphonium bromide
촉매
HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Methyltriphenylphosphonium bromide (187.4 mg, 0.52 mmol) was dissolved in tetrahydrofuran. A 2.62 M solution of n-butyllithium in hexane (0.16 mL, 0.42 mmol) was added dropwise in a nitrogen atmosphere at −78° C., and the mixture was stirred for one hour. After heating to 0° C., a solution of (3S)-3-formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (111 mg, 0.35 mmol) in tetrahydrofuran was added dropwise, and the mixture was stirred for one hour. A saturated ammonium chloride solution was added to the reaction solution, 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 (25% ethyl acetate/hexane) to give 54 mg of the title compound as a yellow oil.

후처리

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

출처 및 근거

ORD 기록
ord-bc8c38d1fe474726a753a4127681b2a4
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618094B2

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