HCID 69748793, compound → (3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester

HRID 1169199Notes

Reaction equation

HRID 1169199 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

Reactant 1

HCID 69748793HCID 69748793, compound

Product 1

HCID 69748878(3R,4R)-4-amino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washThe plug was washed with 20 mL of methanol
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-20e4dc55406742eab09281a38850ef7f
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

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