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 1668348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668348
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

Komponenten

5

Edukt 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

Produkt 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-amineAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-83d555a260a44215886c29c9c1eac2dd
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989442B2

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