Methanol → HCID 68578301, compound

HRID 886972Notes

Reaction equation

HRID 886972 reaction equation
[CH2:1]([N:8]1[C:14](=O)[C:13]2[C:16]([F:21])=[CH:17][CH:18]=[C:19]([Br:20])[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.B.CO.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:14][C:13]2[C:16]([F:21])=[CH:17][CH:18]=[C:19]([Br:20])[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 68577887HCID 68577887, compound

Product 1

HCID 68578301HCID 68578301, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-benzyl-9-bromo-6-fluoro-3,4-dihydro-1,4-benzoxazepine-5 (2H)-one (1.40 g, 4.00 mmol) in tetrahydrofuran (30 ml) was added under ice-cooling 1M borane tetrahydrofuran solution (16.0 ml, 16.0 mmol), and the mixture was stirred at 60° C. for 3 hr. Under ice-cooling, methanol (20 ml) and sodium hydroxide (1.60 g, 40.0 mmol) were added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure. The residue was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (350 mg, 26.1%) as an oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. customThe solvent was evaporated under reduced pressure
  4. additionThe residue was added to water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d3d5f3e6f0e849e8bd012b39f4ae01e0
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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