Methanol → HCID 25122709, compound

HRID 886885Notes

Reaction equation

[CH2:1]([N:8]1[C:14](=O)[C:13]2[CH:16]=[C:17]([Br:20])[CH:18]=[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]=[C:17]([Br:20])[CH:18]=[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]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-benzyl-7-bromo-3,4-dihydro-1,4-benzoxazepine-5 (2H)-one (4.20 g, 12.8 mmol) in tetrahydrofuran (400 ml) was added 1M borane-tetrahydrofuran solution (52.8 ml, 52.8 mmol) and the mixture was stirred at 80° C. for 2 hr. Under ice-cooling, methanol (240 ml) and sodium hydroxide (20.8 g, 519 mmol) were added, and the mixture was stirred at room temperature for 2 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, 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 (2.42 g, 59.5%) as an oil.

Workup

temperatureUnder ice-cooling
stirringthe mixture was stirred at room temperature for 2 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
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-a5c83f201af04d2188b8b38aca4a3587
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247403B2

Reaction notes

Loading…