HCID 69747063, compound → HCID 69750542, compound

HRID 497467Notes

Reaction equation

HRID 497467 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:17]2)=[O:15])[C@@H:10]([NH:30]C(OCC2C=CC=CC=2)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[OH-].[Pd+2].[OH-].CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:17]2)=[O:15])[C@@H:10]([NH2:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69747063HCID 69747063, compound

Product 1

HCID 69750542HCID 69750542, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

In a Paar flask charged with palladium hydroxide (20 wt % on carbon, 0.423 g) was added (3R,4S)-3-benzyloxycarbonylamino-4-[(S)-3-(4-fluoro-benzyl)-piperidine-1-carbonyl]-piperidine-1-carboxylic acid t-butyl ester (1.41 g, 2.53 mmol) and methanol (30 mL). The reaction was hydrogenated at 60 psi with vigorous shaking for 65 hours. The reaction mixture was filtered through a bed of celite and then concentrated in vacuo to give a thick oil (1.19 g) which was used without further purification. 1H NMR (300 MHz, CDCl3), δ: 7.06 (m, 4H), 4.45 (m, 2H), 4.21 (m, 2H), 3.81 (m, 2H), 3.62 (m, 2H), 3.23 (m, 2H), 3.08 (m, 1H), 2.67 (m, 2H), 2.45 (m, 2H), 2.21 (m, 1H), 1.45 (s, 9H). MS (APCI), m+/z: (M+H)+=420.3.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cbcdf7c6a6d41ee8178b4f25c760999
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

Loading…