Boron tribromide → N-Trifluoroacetyl-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepine

HRID 84119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84119
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 22292800HCID 22292800, Verbindung

Produkt 1

HCID 22292790N-Trifluoroacetyl-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepineAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.506 g, 1.76 mmol) in dichloromethane (20 mL) was treated with BBr3 (4.1 mL of a 1.0M solution in CH2Cl2, 4.1 mmol) and stirred overnight while warming to 20 C. The excess BBr3 was quenched with water, and the resulting mixture was diluted with ether (200 mL), washed with Na2CO3 (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 0.460 g of a white solid foam. MS calculated for C13H14F3NO2+H: 274, observed: 274.

Aufarbeitung

  1. temperaturewhile warming to 20 C
  2. customThe excess BBr3 was quenched with water
  3. additionthe resulting mixture was diluted with ether (200 mL)
  4. washwashed with Na2CO3 (100 mL) and brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b153befc247c4a9e873a22bb8aa9a4b1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846906B2

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