Sodium borohydride → HCID 15676054, compound

HRID 1646568Notes

Reaction equation

HRID 1646568 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[C:5]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([F:21])[CH:10]=2)[CH3:8])[N:6]=1.[CH:22]([O-])([O-])OCC.[BH4-].[Na+]>C(O)C>[F:21][C:11]1[CH:10]=[C:9]([CH:7]([C:5]2[N:6]=[C:2]([NH:1][CH3:22])[O:3][CH:4]=2)[CH3:8])[CH:14]=[CH:13][C:12]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 15676053HCID 15676053, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 15676054HCID 15676054, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-(1-(2-fluoro-4-biphenylyl) ethyl)oxazole (1.66 g, 5.88 mmol) and ethyl orthoformate (20 ml) was refluxed for 5 hr and the reaction mixture was evaporated under reduced pressure to a residue. To the residue in ethanol (50 ml) was added sodium borohydride (0.27 g, 7.14 mmol) under cooling, then the mixture was stirred at room temperature for 2 hr. After evaporation, the residue was extracted with ethyl acetate and the extracts were washed with water, dried and then evaporated under reduced pressure to a residue, which was chromatographed and recrystallized to afford 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminooxazole (0.66 g, 40% yield): mp 133.5°-135.0° C.

Workup

  1. temperaturewas refluxed for 5 hr
  2. customthe reaction mixture was evaporated under reduced pressure to a residue
  3. temperatureunder cooling
  4. customAfter evaporation
  5. extractionthe residue was extracted with ethyl acetate
  6. washthe extracts were washed with water
  7. customdried
  8. customevaporated under reduced pressure to a residue, which
  9. customwas chromatographed
  10. customrecrystallized

Sources & evidence

ORD record
ord-127b616aed8e4d2991b5c2a86c914108
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

Loading…