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

HRID 869169Notes

Reaction equation

HRID 869169 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 (6.0 mL). The reaction mixture was stirred for 3 h at room temperature and then quenched by the careful addition of aq. 1M 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%).

Workup

  1. customquenched by the careful addition of aq. 1M 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-d7547846f5e747559e1c4700f2813bd1
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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