HCID 69748793, compound → (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14]C(OCC2C=CC=CC=2)=O)[C@H:10]([C:25]([N:27]2[CH2:32][CH2:31][CH2:30][C@@H:29]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH2:28]2)=[O:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[C@H:10]([C:25]([N:27]2[CH2:32][CH2:31][CH2:30][C@@H:29]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH2:28]2)=[O:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
In a dry 500-mL Paar flask charged with 10 wt % palladium on carbon (0.050 g) and (3R,4R)-4-benzyloxycarbonylamino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (0.25 g, 0.451 mmol) was added methanol (15 mL). The reaction mixture was hydrogenated at 48 psi for 18 hours with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of methanol and the combined filtrates were concentrated in vacuo to give a white solid (0.183 g, 97%). 1H NMR (300 MHz, CDCl3), δ: 8.11 (bs, 2H), 7.15 (m, 2H), 6.97 (t, 2H, J=8), 4.23 (bm, 3H), 3.88 (m, 1H), 3.67 (bs, 1H), 3.13 (m, 1H), 2.60 (bm, 5H), 2.31 (bd, 1H, J=12), 1.74 (bm, 6H), 1.47 (2s, 9H), 1.20 (m, 1H). MS (ESI), m+/z: (M+H)+=420.3.