Methanol → HCID 68577855, compound

HRID 886977Notes

Reaction equation

[CH2:1]([N:8]1[C:14](=O)[C:13]2[CH:16]=[CH:17][C:18]([F:21])=[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.B.O1CCCC1.CO>O1CCCC1>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:16]=[CH:17][C:18]([F:21])=[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

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-benzyl-9-bromo-8-fluoro-3,4-dihydro-1,4-benzoxazepine-5 (2H)-one (3.23 g, 9.22 mmol) in tetrahydrofuran (10 ml) was added under ice-cooling 1M borane-tetrahydrofuran solution (46 ml, 46.1 mmol), and the mixture was refluxed for 2 hr. Under ice-cooling, methanol was added, and the solvent was evaporated under reduced pressure. 6N hydrochloric acid (46 ml) was added, and the mixture was stirred at 100° C. for 1 hr. The solution was basified with 8N sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (2.94 g, 94.8%) as an oil.

Workup

temperaturethe mixture was refluxed for 2 hr
temperatureUnder ice-cooling
customthe solvent was evaporated under reduced pressure
addition6N hydrochloric acid (46 ml) was added
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-235d3023e7ea495fb050233b70bfe0d4
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247403B2

Reaction notes

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