Sodium borohydride → HCID 118093796, compound

HRID 1057019Notes

Reaction equation

HRID 1057019 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:7][C:6]=2[C:17]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>C(O)C.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:7][C:6]=2[C:17]=1[O:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 118093963HCID 118093963, compound

Product 1

HCID 118093796HCID 118093796, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 6-bromo-5-phenoxy-3-phenyl-2H-1,4-benzoxazine (0.0692 g, 0.182 mmol) in ethanol (1.20 mL) and water (0.240 mL) was treated with sodium tetrahydroborate (13.8 mg, 0.364 mmol) and stirred at 90° C. for 2 h. The reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 30% EtOAc/hexanes) gave the desired product (67.3 mg, 97%) as a colorless oil. LCMS calculated for C20H17BrNO2 (M+H)+: m/z=382.0, 384.0. found: 382.0, 384.0.

Workup

  1. customLayers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customPurification by flash column chromatography (100% hexanes to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5461d8b30fc341678aab6d98af4d8c3b
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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