Methanol → 4-Benzyl-8-bromo-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine
Reaction equation
[CH2:1]([N:8]1[C:14](=O)[C:13]2[CH:16]=[CH:17][C:18]([Br:20])=[CH:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.CO.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:16]=[CH:17][C:18]([Br:20])=[CH:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 4-benzyl-8-bromo-3,4-dihydro-1,4-benzoxazepine-5 (2H)-one (4.50 g, 13.5 mmol) in tetrahydrofuran (45 ml) was added 1M borane-tetrahydrofuran solution (54 ml, 54.0 mmol), and the mixture was stirred at 65° C. for 4 hr. Under ice-cooling, methanol (135 ml) and sodium hydroxide (11.7 g, 294 mmol) were added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure. The residue was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the desired product (4.30 g, 100%) as an oil.
Workup
- temperatureUnder ice-cooling
- stirringthe mixture was stirred at room temperature for 1 hr
- customThe solvent was evaporated under reduced pressure
- additionThe residue was poured into water
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-aa36567726f14cf7980d6e00cbd6206e
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247403B2
Reaction notes
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