4-benzyloxy-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one → HCID 58042802, compound

HRID 564042Notes

Reaction equation

HRID 564042 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[C:11](=[O:29])[CH:10]=1)C1C=CC=CC=1>CO.[Rh]>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:19][CH:18]=2)[C:11](=[O:29])[CH:10]=1

Participants

4

Reactant 1

HCID 670066024-benzyloxy-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one

Product 1

HCID 58042802HCID 58042802, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

To 1.20 g (3.09 mmol) 4-benzyloxy-1-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 1.4) in 80 mL MeOH is added 400 mg Rh/C. The reaction mixture is stirred under a hydrogen atmosphere of 3500 hPa at RT for 11 h. The catalyst is removed by filtration and the solvent is evaporated. The residue is purified by reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated
  3. customThe residue is purified by reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-4323dd1e3b1645e89dbdf64ecbfb4182
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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