Sodium borohydride → HCID 19434450, compound

HRID 889033Notes

Reaction equation

HRID 889033 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:7]1=[O:21])=O)C.[BH4-].[Na+]>C(O)C>[OH:3][CH2:4][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)[C:7]1=[O:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 574296622-Oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

Product 1

HCID 19434450HCID 19434450, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
12.5 °C

Procedure

A mixture of 2-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester obtained in step 2 (0.5 g, 1.6 mmol) and ethanol were cooled to 10-15° C. Sodium borohydride (0.126 g, 3.3 mmol) was added portion wise over a period of 20 min and the reaction mixture was stirred for 3.5 hrs at 20-25° C. The organic volatiles were evaporated and the residue was taken into brine solution (15 ml). The aqueous layer was extracted with ethyl acetate, dried over Na2SO4 and evaporated to obtain brown semi solid which was purified by preparative TLC to afford 3-Hydroxymethyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one as a colorless oil (0.177 g, 43%).

Workup

  1. customThe organic volatiles were evaporated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto obtain brown semi solid which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-5ff374fc80a8489eb5aaf95d754e862a
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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