Hydrogen Bromide → HCID 22406762, compound

HRID 440482Notes

Reaction equation

HRID 440482 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24]C)=[C:19]([O:22]C)[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:26])[CH2:11][CH2:10][CH2:9]1.Br>C(O)(=O)C>[BrH:1].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:24])=[C:19]([OH:22])[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:26])[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22406883HCID 22406883, compound

Product 1

HCID 22406762HCID 22406762, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (-)-1-[1-(2-bromophenyl)cyclobutyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1.46 g), 48% aqueous hydrobromic acid (20 ml) and glacial acetic acid (20 ml) was heated under reflux for 5 hours. The solvent was removed by evaporation and the residue dried by repeated azeotropic distillation with propan-2-ol. The residue was dissolved in propan-2-ol and precipitated with ether. The resulting solid was dried in vacuo at 45° C. to yield (+)-1-[1-(2-bromo-phenyl)cyclobutyl] -6,7-dihydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline hydrobromide [m.p. 207°-209° C. (dec)] which had a specific optical rotation αD of +38.2°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent was removed by evaporation
  4. customthe residue dried
  5. distillationdistillation with propan-2-ol
  6. dissolutionThe residue was dissolved in propan-2-ol
  7. customprecipitated with ether
  8. customThe resulting solid was dried in vacuo at 45° C.

Sources & evidence

ORD record
ord-f15a157555c34a9eafb7d155fe9c5476
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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