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

HRID 1776969
Notes
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Reaction equation

HRID 1776969 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 131734762HCID 131734762, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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%)

Workup

  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)

Sources & evidence

ORD record
ord-e3b69b10681f4c60b843ef514096fc23
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266820B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes