HCID 69748748, compound → HCID 69748549, compound

HRID 497475Notes

Reaction equation

HRID 497475 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 69748748HCID 69748748, compound

Product 1

HCID 69748549HCID 69748549, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a dry 500-mL Paar flask charged with palladium (10 wt % Pd, dry basis, on carbon, 31 mg) was added methanol (10 mL) and (3S,4R)-4-benzyloxycarbonylamino-3-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (150 mg, 2.08 mmol). The reaction mixture was hydrogenated at 45 psi for 20.5 hours with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of ethanol and the combined filtrates were concentrated in vacuo to give a colorless oil (111 mg, 98%). 1H NMR (300 MHz, CDCl3), δ: 8.75 (bs, 2H), 7.09 (m, 2H), 6.97 (m, 2H), 4.30 (m, !H), 4.01 (m, 2H), 3.70 (m, 2H), 3.25 (m, 1H), 3.10 (m, 1H), 2.75 (m, 1H), 2.48 (m, 4H), 1.82 (m, 5H), 1.42 (s, 9H), 1.21 (m, 2H). 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 ethanol
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-220445cd0496411585bf39cefdf9b445
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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