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

HRID 47126Notes

Reaction equation

HRID 47126 reaction equation
[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>C(Cl)(Cl)Cl>[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

Participants

3

Reactant 1

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

Product 1

HCID 5284592Nabilone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Evaporation of the solvent from eluates shown by thin layer chromatography to contain a different component afforded 55 mg. of (-)-cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one. [α]20D-50° (c=1.0, CHCl3).

Workup

  1. customEvaporation of the solvent from eluates
  2. customafforded 55 mg

Sources & evidence

ORD record
ord-964da95d25024bbb9be94e285f40e4af
Source dataset
uspto-grants-1979_11
Patent number
US04176233

Reaction notes

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