Hydrogen Bromide → (-)-(cis)-7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-amine

HRID 1668348Notes

Reaction equation

HRID 1668348 reaction equation
Br.[Br:2][C:3]1[C:26]([F:27])=[CH:25][C:6]2[O:7][C:8]3[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH:16]C(=O)OC)[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1.[OH-].[Na+]>C(O)(=O)C>[Br:2][C:3]1[C:26]([F:27])=[CH:25][C:6]2[O:7][C:8]3[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=3[C@H:10]3[C@H:15]([NH2:16])[CH2:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 86619612Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

Product 1

HCID 67358773(-)-(cis)-7-bromo-8-fluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-amineYield 91.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of acetic acid (40 mL) and hydrogen bromide (48%, 20 mL) was added to 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 (20.2 g, 48 mmol) and stirred overnight at 100° C. After cooling down the reaction mixture was poured into a cold 1M NaOH solution. It was extracted with CH2Cl2 and the organic layer was washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to yield the crude title compound (15.9 g, 91%) which was used without further purification. (m/z)=363+365 (M+H)+.

Workup

  1. temperatureAfter cooling down the reaction mixture
  2. extractionIt was extracted with CH2Cl2
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-83d555a260a44215886c29c9c1eac2dd
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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