Phenylmethyl(2R,5S)-2-methyl-5-[(phenylamino)carbonyl]-1-piperidinecarboxylate → (3S,6R)-6-Methyl-N-phenyl-3-piperidinecarboxamide

反応式

[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH2:4][N:3]1C(OCC1C=CC=CC=1)=O>CCOC(C)=O.CCO.[Pd]>[CH3:1][C@H:2]1[NH:3][CH2:4][C@@H:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:6][CH2:7]1

参加物

実験手順

A solution of phenylmethyl(2R,5S)-2-methyl-5-[(phenylamino)carbonyl]-1-piperidinecarboxylate (21 g, 59.6 mmol) in EtOAc (250 mL) and EtOH (250 mL) was degassed. Pd/C (10%, 6.34 g, 5.96 mmol) was added and then H2 was bubbled through the mixture. The reaction mixture was stirred at room temperature under H2 balloon overnight. The mixture was filtered through a pad of celite, and concentrated in vacuo to afford the crude title compound (12 g). LC-MS (ES) m/z=219 [M+H]+.