Sodium borohydride → HCID 86759253, compound

HRID 479873Notes

Reaction equation

HRID 479873 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]([CH3:15])[CH3:14])[C@@:11](O)([C:16]([F:19])([F:18])[F:17])[O:10]C1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:12]([CH:13]([CH3:14])[CH3:15])[C@H:11]([OH:10])[C:16]([F:19])([F:18])[F:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69537565HCID 69537565, compound

Product 1

HCID 86759253HCID 86759253, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(4S,5S)-5-Hydroxy-4-isopropyl-5-trifluoromethyl-1,3-oxazolidine-3-carboxylic acid t-butyl ester (4.51 g, 0.015 mol) obtained in Example 6 was dissolved in methanol (50 ml), and thereto was slowly added sodium borohydride (500 mg, 0.013 mol) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction solution was added saturated brine, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1) and recrystallized from n-hexane/ethyl acetate to give the desired compound (2.1 g, yield: 51%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1)
  6. customrecrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-3112dd1b08af4ebca2c5f7c5ab24792e
Source dataset
uspto-grants-2003_11
Patent number
US06646150B1

Reaction notes

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