Water → HCID 21920050, compound

HRID 1823035Notes

Reaction equation

HRID 1823035 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=O.[BH4-].[Na+].O>C1COCC1>[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[F:25])[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:7]2[CH2:6][CH:5]([CH2:3][OH:2])[CH2:9][C:8]2=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68615133HCID 68615133, compound

Product 1

HCID 21920050HCID 21920050, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (5.54 mmol) (RS)-1-[4-(3,4-Difluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester is dissolved in 50 ml THF. 1.05 g (27.7 mmol) of sodium borohydride is added and the reaction mixture boiled under reflux for 24 hours. Water is added and the product is extracted with ethyl acetate to yield 1.68 g (91%) of a yellowish solid. MS: m/e=334.3 (M+H)+.

Workup

  1. temperatureunder reflux for 24 hours
  2. extractionthe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-5db96396122447028401666423f0dd42
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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