Toluene → HCID 86643171, compound

HRID 1808317Notes

Reaction equation

HRID 1808317 reaction equation
[C:1](O)(=O)C(O)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C@:18]2([CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH2:21][CH2:20][NH:19]2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[OH-].[NH4+].C1(C)C=CC=CC=1.[I:50]C>O>[I-:50].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C@:18]2([CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]3[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=3)[CH2:21][CH2:20][NH+:19]2[CH3:1])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 14923Ammonium HydroxideHCID 67538267HCID 67538267, compound

Product 1

HCID 86643171HCID 86643171, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethylisoquinoline oxalate (7.0 g, 0.0125 moles), prepared as described in example 1, was dissolved in water (50 ml) and 25% aqueous ammonium hydroxide solution was added to produce a pH in the range of 9-10. Toluene (100 ml) was added and the mixture was stirred for 15 minutes at ambient temperature. The upper organic layer was separated and washed with 10% sodium chloride solution. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure to afford a solid residue. Iodomethane (30 ml, 0.482 moles) was added to the residue and the mixture was stirred to obtain a solution and kept at ambient temperature overnight. The resulting precipitate was collected by filtration, washed with diethyl ether and dried at room temperature to afford a mixture of 81.5% of the cis and 18.5% of the trans isomers of (1R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-2-tert-butoxycarbonylethyl-isoquinolinium iodide (5.5 g; 72% yield).

Workup

  1. customto produce a pH in the range of 9-10
  2. customThe upper organic layer was separated
  3. washwashed with 10% sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customto afford a solid residue
  7. stirringthe mixture was stirred
  8. customto obtain a solution
  9. waitkept at ambient temperature overnight
  10. filtrationThe resulting precipitate was collected by filtration
  11. washwashed with diethyl ether
  12. customdried at room temperature
  13. customto afford

Sources & evidence

ORD record
ord-bc6ae21dab6a4aeab3e3112d7b089b5a
Source dataset
uspto-grants-2013_01
Patent number
US08357807B2

Reaction notes

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