Sodium borohydride → HCID 67115789, compound

HRID 1258817Notes

Reaction equation

HRID 1258817 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[C:12]=2[CH:23]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 583408561-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 67115789HCID 67115789, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (8.6 g, 19.8 mmol) in ethanol (40 mL) was added NaBH4 (1.5 g, 39.0 mmol) portion wise and the reaction mixture was stirred overnight. Excess of NaBH4 was quenched by adding aq. NH4Cl, and ethanol was evaporated. The residue was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine (40 mL) and dried over sodium sulphate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (6.1 g).

Workup

  1. customExcess of NaBH4 was quenched
  2. additionby adding aq. NH4Cl, and ethanol
  3. customwas evaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic layer was separated
  6. washwashed with brine (40 mL)
  7. dry with materialdried over sodium sulphate
  8. customCrude product obtained
  9. customafter evaporation of solvent
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-542a7fe9b0c1410d9a6c87d7ed647015
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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