Sodium borohydride → HCID 86689561, compound

HRID 1853898Notes

Reaction equation

HRID 1853898 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:25])[C@H:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])[CH3:16])C1C=CC=CC=1.[BH4-].[Na+]>C1COCC1.O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C@H:15]([CH3:16])[CH2:14][OH:25])=[C:18]([F:24])[CH:19]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68229193HCID 68229193, compound

Product 1

HCID 86689561HCID 86689561, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ((S)-4-benzyl-3-((S)-2-(4-bromo-2-fluorophenyl)propanoyl)oxazolidin-2-one) (1.7 g, 4.2 mmol) in THF (12 mL) was added a solution of sodium borohydride (700 mg, 21 mmol) in water (2 mL). The reaction mixture was stirred for 3 h at room temperature. The excess hydride was quenched by slow addition of aqueous hydrochloric acid (1 N, ca. 2.9 mL). The mixture was further diluted with water (10 mL) and extracted with ethyl acetate (1×30 mL). The combined organics were washed with brine (2×10 mL), dried over sodium sulfate, and evaporated under vacuum. The residue was purified by flash chromatography of the residue afforded the desired product (0.8 g, 82%) as light yellow oil: ESI MS m/z 234 [C9H10BrFO+H]+

Workup

  1. customThe excess hydride was quenched by slow addition of aqueous hydrochloric acid (1 N, ca. 2.9 mL)
  2. additionThe mixture was further diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (1×30 mL)
  4. washThe combined organics were washed with brine (2×10 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue was purified by flash chromatography of the residue

Sources & evidence

ORD record
ord-d6487a82931443fd8b9106144b356351
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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