Bromhydrol → Nabilone

HRID 972941ノート

反応式

HRID 972941 の反応式
[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

参加物

4

反応物 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

生成物 1

HCID 5284592Nabilone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
24 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe71dd87d364406481a65cee04caf5a3
出典データセット
uspto-grants-1977_10
特許番号
US04054582

反応ノート

読み込み中…