Water → methyl (+/-)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

HRID 1668356Notes

Reaction equation

B.[Br:2][C:3]1[C:28]([F:29])=[CH:27][C:6]2[O:7][C:8]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:9]=3[C@H:10]3[C@H:15]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH2:14][CH2:13][C:12](=O)[N:11]3[C:5]=2[CH:4]=1.O>C1COCC1.C(OCC)(=O)C>[Br:2][C:3]1[C:28]([F:29])=[CH:27][C:6]2[O:7][C:8]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:9]=3[C@H:10]3[C@H:15]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Borane (1.0 M in THF, 38.3 mL, 38.3 mmol) was added dropwise to a stirred solution of methyl (±)-(cis)-(7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-4-oxo-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate (38.2 mmol) in THF (200 mL). The resulting mixture was stirred at 30° C. for 1 h. Subsequently, water was added dropwise until evolution of gas ceased. The resulting mixture was stirred for 1 h and then diluted with ethyl acetate (300 mL) and washed with brine. After drying (Na2SO4) the solvent was evaporated under reduced pressure to yield the crude title compound (16.7 g, 100%). (m/z)=439+441 (M+H)+.

Workup

stirringThe resulting mixture was stirred for 1 h
washwashed with brine
dry with materialAfter drying (Na2SO4) the solvent
customwas evaporated under reduced pressure

Sources & evidence

ORD record: ord-a157d25e50324c6e8598cc2405a31107
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989442B2

Reaction notes

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