Sodium borohydride → (S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile

HRID 503921Notes

Reaction equation

HRID 503921 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([C:14](N2[C@@H](C(C)C)COC2=O)=[O:15])[CH2:11][C:12]#[N:13])=[C:6]([O:25][CH3:26])[CH:5]=1.OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O.C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([CH2:14][OH:15])[CH2:11][C:12]#[N:13])=[C:6]([O:25][CH3:26])[CH:5]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 66877211(S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrileHCID 86586342KHSO4 Na2SO4

Product 1

HCID 66876540(S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrileYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium borohydride (389 mg) in water (1.82 mL) was added to a solution of (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile (749 mg, 1.895 mmol) in THF (6 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for three hours. The reaction mixture was cooled to 0° C. and a solution of 10% KHSO4/Na2SO4 was carefully added. After the gas evolution stopped, the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 7/3) to give 470 mg (92% yield) of (S)-3-(4-bromo-2-methoxy-phenyl)-4-hydroxy-butyronitrile.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 7/3)

Sources & evidence

ORD record
ord-f22e4a1567ea4a959e34c5a9adc7a720
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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