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

反応式

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

参加物

実験手順

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%)