Bromhydrol → Nabilone

HRID 972941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972941
[OH:1][C:2]1[C:11]2[C@H:10]3[CH2:12][C:13](=[O:16])[CH2:14][CH2:15][C@H:9]3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1.[Br-].[Al+3].[Br-].[Br-]>ClCCl>[OH:1][C:2]1[C:11]2[C@@H:10]3[CH2:12][C:13](=[O:16])[CH2:14][CH2:15][C@H:9]3[C:8]([CH3:17])([CH3:18])[O:7][C:6]=2[CH:5]=[C:4]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1

Komponenten

4

Edukt 2

HCID 166749BromhydrolHCID 86735145cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one

Produkt 1

HCID 5284592Nabilone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
24 °C

Versuchsvorschrift

To a solution of 1.0 g. of dl-cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one in 40 ml. of dichloromethane was added in one portion 1.0 g. of aluminum bromide. The reaction mixture was stirred for five hours at 24° C., and then was washed with 1N hydrochloric acid solution and with water. The reaction mixture was dried and the solvent was removed by evaporation under reduced pressure, thus providing dl-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.

Aufarbeitung

  1. washwas washed with 1N hydrochloric acid solution and with water
  2. customThe reaction mixture was dried
  3. customthe solvent was removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fe71dd87d364406481a65cee04caf5a3
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04054582

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