rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one → 5-(2,6-Dimethoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

HRID 594404Notes

Reaction equation

HRID 594404 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[C:14](=[O:28])[C:13](=[CH2:29])[CH2:12]1>CO>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH:11]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=2)[C:14](=[O:28])[CH:13]([CH3:29])[CH2:12]1

Participants

3

Reactant 1

HCID 86695633rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

Product 1

HCID 690801865-(2,6-Dimethoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of rac-(S*)-5-(2,6-dimethoxyphenyl)-3-methylene-1-(4-(trifluoromethoxy)-benzyl)pyrrolidin-2-one (310 mg; 0.76 mmol), and 10% Pd(C) (62 mg; 20% in mass) in anh. MeOH (3 ml) was stirred at rt, under hydrogen atmosphere (1 atm), for 60 h. Filtration over a pad of celite, concentration to dryness under reduced pressure, and subsequent purification by FC (DCM/MeOH=30/1) afforded rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-methyl-1-(4-(trifluoromethoxy)-benzyl)pyrrolidin-2-one as an orange oil. LC-MS (conditions A): tR=0.94 min.; [M+H]+: 410.27 g/mol.

Workup

  1. filtrationFiltration
  2. concentrationover a pad of celite, concentration to dryness
  3. customunder reduced pressure, and subsequent purification by FC (DCM/MeOH=30/1)

Sources & evidence

ORD record
ord-66617c700fa84c10b3406ef8d3990f78
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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