HCID 69750535, compound → HCID 69747091, compound

HRID 497473Notes

Reaction equation

HRID 497473 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C@@H](C2C=CC=CC=2)C)[C@@H:10]([C:23]([OH:25])=[O:24])[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]([NH2:14])[C@@H:10]([C:23]([OH:25])=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69750535HCID 69750535, compound

Product 1

HCID 69747091HCID 69747091, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

In a dry 500-mL Paar flask charged with Palladium hydroxide (20 wt % Pd, dry basis, on carbon, 0.22 g) was added methanol (50 mL) and (3S,4R)-4-[(R)-1-Phenyl-ethylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (2.11 g, 6.05 mmol). The reaction mixture was hydrogenated at 53 psi for 42 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 (1.32 g, 89%). 1H NMR (300 MHz, CDCl3), δ: 4.38 (bd, J=12, 1H), 4.16 (m, 1H), 3.30 (m, 1H), 2.70 (m, 2H), 1.90-2.40 (m, 5H), 1.45 (s, 9H). MS (ESI), m+/z: (M+H)+=245.1.

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-8589607115c34867b0faafe3b9d85997
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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