Boron tribromide → Nabilone

HRID 1075307Notes

Reaction equation

HRID 1075307 reaction equation
C[O:2][C:3]1[C:12]2[C@@H:11]3[CH2:13][C:14](=[O:17])[CH2:15][CH2:16][C@H:10]3[C:9]([CH3:19])([CH3:18])[O:8][C:7]=2[CH:6]=[C:5]([C:20]([CH3:28])([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:12]2[C@@H:11]3[CH2:13][C:14](=[O:17])[CH2:15][CH2:16][C@H:10]3[C:9]([CH3:18])([CH3:19])[O:8][C:7]=2[CH:6]=[C:5]([C:20]([CH3:27])([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13188551HCID 13188551, compound

Product 1

HCID 5284592Nabilone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dl-trans-1-methoxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one (prepared as described in Example 1) and boron tribromide in dichloromethane is stirred for about eight hours at about 40° C. The reaction mixture is then washed with water, dried, and the solvent is removed by evaporation under reduced pressure to give 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. This compound is known as nabilone and is especially useful in the treatment of nausea in humans.

Workup

  1. washThe reaction mixture is then washed with water
  2. customdried
  3. customthe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ad7ec997f6cb413ba356e9d8fd060bb6
Source dataset
uspto-grants-1983_07
Patent number
US04395560

Reaction notes

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