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Cyclohexene → (2S,3aS,6aS)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-octahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 1776969
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HRID 1776969 반응식
C([C@@:8]1([C:33]([O-:35])=[O:34])[N:12]([C:13]([O:15][CH2:16][CH:17]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[C@H:11]2[CH2:30][CH2:31][CH2:32][C@H:10]2[CH2:9]1)C1C=CC=CC=1.C1CCCCC=1>CCO.[Pd]>[CH:28]1[C:29]2[CH:17]([CH2:16][O:15][C:13]([N:12]3[C@H:8]([C:33]([OH:35])=[O:34])[CH2:9][C@@H:10]4[CH2:32][CH2:31][CH2:30][C@H:11]34)=[O:14])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]=2[CH:25]=[CH:26][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 8079CyclohexeneHCID 131734762HCID 131734762, 화합물

생성물 1

HCID 68590419(2S,3aS,6aS)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-octahydrocyclopenta[b]pyrrole-2-carboxylic acid수율 37%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of (2S,3aS,6aS)-1-(9H-fluoren-9-yl)methyl 2-benzylhexahydrocyclopenta[b]pyrrole-1,2(2H)-dicarboxylate (1.68 g, 3.6 mmol) in EtOH 95% (15 ml) was added Palladium on carbon 10% (0.2 g, 0.18 mmol) and cyclohexene (3.5 ml, 36 mmol). The resulting mixture was refluxed for 7 h. The solvent was evaporated and the crude was diluted with CH2Cl2 (20 ml). The suspension was filtered on celite the organic phase was evaporated under vacuum. The residue was purified by flash chromatography (CH2Cl2/CH3CN 50:50) to give the title compound as a white foam (0.5 g, 37%)

후처리

  1. temperatureThe resulting mixture was refluxed for 7 h
  2. customThe solvent was evaporated
  3. additionthe crude was diluted with CH2Cl2 (20 ml)
  4. filtrationThe suspension was filtered on celite the organic phase
  5. customwas evaporated under vacuum
  6. customThe residue was purified by flash chromatography (CH2Cl2/CH3CN 50:50)

출처 및 근거

ORD 기록
ord-e3b69b10681f4c60b843ef514096fc23
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266820B2

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