Sodium borohydride → (S)-2-(4-Fluorophenyl)propan-1-ol

HRID 922695Notes

Reaction equation

HRID 922695 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:24])[C@H:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH3:16])C1C=CC=CC=1.[BH4-].[Na+]>C1COCC1.O>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C@H:15]([CH3:16])[CH2:14][OH:24])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67452410(S)-4-Benzyl-3-((S)-2-(4-fluorophenyl)propanoyl)oxazolidin-2-one

Product 1

HCID 12969931(S)-2-(4-Fluorophenyl)propan-1-olYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a room-temperature solution of (S)-4-benzyl-3-((S)-2-(4-fluorophenyl) propanoyl)oxazolidin-2-one (1.8 g, 5.5 mmol, 1.0 equiv) in THF (18 mL) was added a solution of NaBH4 (1.0 g, 26.4 mmol, 4.8 equiv) in water (6 mL). The reaction mixture was stirred for 3 h at room temperature and then quenched by the careful addition of aq. 1 M HCl. The reaction mixture was diluted with water and ethyl acetate. The layers were separated and the organic layer was subsequently washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (10-75% EtOAc/Hexanes) provided the title compound (0.824 g, 97%) which was characterized by 1H NMR.

Workup

  1. customquenched by the careful addition of aq. 1 M HCl
  2. additionThe reaction mixture was diluted with water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer was subsequently washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography (10-75% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b1bb784977e4460f896e1b0e0768ad77
Source dataset
uspto-grants-2016_03
Patent number
US09278962B2

Reaction notes

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