Hydrogen Bromide → (-)-(cis)-7-bromo-8,12-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine
Reaktionsgleichung
Br.[Br:2][C:3]1[C:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[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:27]([F:28])=[CH:26][C:6]2[O:7][C:8]3[CH:24]=[C:23]([F:25])[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]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of acetic acid (80 mL) and hydrogen bromide (48%, 40 mL) was added to 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 (38.2 mmol), and the mixture stirred overnight at 100° C. After cooling down the reaction mixture was poured into a cold 1N NaOH solution (pH 9). It was extracted with ethyl acetate and the organic layer was washed with brine, dried (Na2SO4) and the solvent was evaporated under reduced pressure to yield the crude title compound (12.7 g, 87%) which was used without further purification. (m/z)=381+383 (M+H)+.
Aufarbeitung
- temperatureAfter cooling down the reaction mixture
- extractionIt was extracted with ethyl acetate
- washthe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- customthe solvent was evaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-19cefacc63994b60876e97209bb19297
- Quelldatensatz
- uspto-grants-2011_08
- Patentnummer
- US07989442B2
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