1-(4-(Benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one → 5-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one

HRID 594666Notes

Reaction equation

HRID 594666 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][N:14]2[CH:18]([C:19]3[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:20]=3[O:27][CH3:28])[CH2:17][CH2:16][C:15]2=[O:29])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO>[CH3:28][O:27][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH3:26])[C:19]=1[CH:18]1[N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:31][CH:30]=2)[C:15](=[O:29])[CH2:16][CH2:17]1

Participants

3

Reactant 1

HCID 690857521-(4-(Benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one

Product 1

HCID 690819375-(2,6-Dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(4-(benzyloxy)benzyl)-5-(2,6-dimethoxyphenyl)pyrrolidin-2-one (316 mg; 0.75 mmol), and 10% Pd(C) (90 mg) in anh. MeOH (4 ml) was stirred at rt, under hydrogen atmosphere (1 atm), for 24 h. Filtration over a pad of celite, concentration to dryness under reduced pressure, and additional drying under HV afforded 5-(2,6-dimethoxyphenyl)-1-(4-hydroxybenzyl)pyrrolidin-2-one as a colorless solid (120 mg; 48%). LC-MS (conditions A): tR=0.67 min.; [M+H]+: 328.10 g/mol.

Workup

  1. filtrationFiltration
  2. concentrationover a pad of celite, concentration to dryness under reduced pressure
  3. customadditional drying under HV

Sources & evidence

ORD record
ord-a9367c9b7c644f188dec227cc67a75bd
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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