Hydrochloric Acid → Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

HRID 1668347Notes

Reaction equation

HRID 1668347 reaction equation
B.O1CCCC1.[Br:7][C:8]1[C:32]([F:33])=[CH:31][C:11]2[O:12][C:13]3[CH:30]=[CH:29][CH:28]=[CH:27][C:14]=3[C@H:15]3[C@H:20]([NH:21][C:22](=[O:25])[O:23][CH3:24])[CH2:19][CH2:18][C:17](=O)[N:16]3[C:10]=2[CH:9]=1.Cl>C1COCC1.C(OCC)(=O)C>[Br:7][C:8]1[C:32]([F:33])=[CH:31][C:11]2[O:12][C:13]3[CH:30]=[CH:29][CH:28]=[CH:27][C:14]=3[C@H:15]3[C@H:20]([NH:21][C:22](=[O:25])[O:23][CH3:24])[CH2:19][CH2:18][CH2:17][N:16]3[C:10]=2[CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 86619611Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-4-oxo-2H-dibenzo [b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

Product 1

HCID 86619612Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamateYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Borane-tetrahydofuran complex (1.0 M in THF, 970 mL, 970 mmol) was added dropwise to a stirred solution of methyl (±)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-4-oxo-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate (105.2 g, 242 mmol) in THF (1 L). The resulting mixture was stirred at ambient temperature for 3 h. Subsequently, hydrochloric acid (1M) was added dropwise until evolution of gas ceased (±550 mL). The resulting mixture was stirred for 1 h and then diluted with ethyl acetate; the organic layer was washed with water and brine. After drying (MgSO4) the solvent was evaporated under reduced pressure to yield the crude title compound (98.5 g, 97%). (m/z)=421+423 (M+H)+.

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. washthe organic layer was washed with water and brine
  3. dry with materialAfter drying (MgSO4) the solvent
  4. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-8e8dbdc4568444dfba0844412061032d
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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