Hydrogen Bromide → HCID 22406846, compound

HRID 440487Notes

Reaction equation

HRID 440487 reaction equation
[Cl: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]([F:23])=[C:19]([OH:22])[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:24])[CH2:11][CH2:10][CH2:9]1.[BrH:25]>CC(O)C>[BrH:25].[Cl: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]([F:23])=[C:19]([OH:22])[CH:20]=3)[CH2:15][CH2:14][N:13]2[CH3:24])[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22406724HCID 22406724, compound

Product 1

HCID 22406846HCID 22406846, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-[1-(2-Chlorophenyl)cyclobutyl]-6-fluoro-7-hydroxy-2methyl-1,2,3,4-tetrahydroisoquinoline (8.0 g liberated from the salt prepared as described in Example 24) was resolved by chiral preparative high performance liquid chromatography on a Chiralcel OD column eluted with an 80:20 mixture of hexane and ethanol. The residue formed by the removal of the solvent from fraction 1 was dissolved in propan-2-ol and treated with 48% aqueous hydrobromic acid to yield (+)-1-[1-(2-chlorophenyl)cyclobutyl]-6-fluoro-7-hydroxy-2-methyl-1,2,3,4 -tetrahydroisoquinoline hydrobromide which had a specific optical rotation αD of +9.64° , m.p. 242°-245° C. (dec). Yield 3.63 g.

Workup

  1. customprepared
  2. washeluted with an 80:20 mixture of hexane and ethanol
  3. customThe residue formed by the removal of the solvent from fraction 1

Sources & evidence

ORD record
ord-66641768bc7b4fba8c24564d08156b52
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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