Sodium borohydride → rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

HRID 594399Notes

Reaction equation

HRID 594399 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](=[O:29])[CH2:12]1.[BH4-].[Na+]>CCO>[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:25])([F:26])[F:27])=[CH:19][CH:18]=2)[C:14](=[O:28])[CH:13]([OH:29])[CH2:12]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 690846265-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

Product 1

HCID 69082591rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione (1.514 g; 3.69 mmol) in anh. EtOH (20 ml) was treated with NaBH4 (700 mg; 18.49 mmol), and the mixture was stirred at rt, under nitrogen, for 2 h. After concentration to dryness under reduced pressure, the resulting residue was treated with 1 M aq. HCl and with water. After extractions with DCM, the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording rac-(3S*,5S*)-5-(2,6-dimethoxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one as a colorless foam. LC-MS (conditions A): tR=0.81 min.; [M+H]+: 412.27 g/mol.

Workup

  1. concentrationAfter concentration to dryness under reduced pressure
  2. additionthe resulting residue was treated with 1 M aq. HCl and with water
  3. extractionAfter extractions with DCM
  4. dry with materialthe mixed organic layers were dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-87ddbbd11bb94b7ca9cf86aba3c6a1e1
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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