Boron tribromide → HCID 69823504, compound

HRID 382812Notes

Reaction equation

HRID 382812 reaction equation
Cl.[Br:2][C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]2[C@@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:16])[CH2:14]3)[CH2:9][C:8](=[O:17])[C:7]=2[C:18]=1[O:19]C.B(Br)(Br)Br>C(Cl)Cl>[Br:2][C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]2[C@@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:16])[CH2:14]3)[CH2:9][C:8](=[O:17])[C:7]=2[C:18]=1[OH:19]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86757544HCID 86757544, compound

Product 1

HCID 69823504HCID 69823504, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.421 g (1:11 mmol) of trans-8-bromo-7,9-dimethoxy-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h] isoquinolin-6-one hydrochloride in 40 ml of methylene chloride was treated at −70° with 1.23 ml of a 1M BBr3 solution in methylene chloride. After 15 minutes the cooling bath was removed. After the solution had reached room temperature it was stirred for one hour, subsequently poured on to 80 ml of ice/sat. sodium hydrogen carbonate solution and extracted three times with 60 ml of methylene chloride. The organic phase was dried (Na2SO4), filtered and evaporated. Chromatography (silica gel, methylene chloride/methanol 9:1) yielded 0.315 g (83%) of trans-8-bromo-7-hydroxy-9-methoxy-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one, which was converted with HCl in methanol into the hydrochloride with m.p. 257-259°.

Workup

  1. customAfter 15 minutes the cooling bath was removed
  2. customhad reached room temperature
  3. additionsubsequently poured on to 80 ml of ice/
  4. extractionsodium hydrogen carbonate solution and extracted three times with 60 ml of methylene chloride
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-055a89ceba4b4dc7adc363293afd5ad4
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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