Methyl iodide → HCID 86643171, compound

HRID 2067923Notes

Reaction equation

HRID 2067923 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].C(=O)(O)[O-].[Na+].ClCCl.[I:49]C>O.C(OCC)C>[I-:49].[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

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 67538267HCID 67538267, compound

Product 1

HCID 86643171HCID 86643171, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

(1R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-tert-butoxycarbonylethylisoquinoline oxalate (1.0 g, 0.00178 moles) was dissolved in water (10 ml) and saturated aqueous sodium bicarbonate solution was added to produce a pH in the range of 9-10. Dichloromethane (20 ml) was added and the mixture was stirred for 15 minutes at ambient temperature. The upper organic layer was separated and the aqueous layer was extracted three times with dichloromethane (3×20 ml). The combined organic layer was dried over magnesium sulfate. The organic layer was evaporated under reduced pressure to afford a residual oil. Iodomethane (8 ml, 0.128 moles) was added to the oily residue and the mixture was stirred to obtain a solution and kept at room temperature overnight. The reaction mixture was added to diethyl ether (50 ml) to afford a suspension, which was stirred at ambient temperature for 30 minutes. The thus formed solid was collected by filtration, washed with diethyl ether (2×5 ml) and dried to afford a mixture of 70% of the cis and 30% 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 (0.95 g; 89% yield).

Workup

  1. customto produce a pH in the range of 9-10
  2. customThe upper organic layer was separated
  3. extractionthe aqueous layer was extracted three times with dichloromethane (3×20 ml)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. customThe organic layer was evaporated under reduced pressure
  6. customto afford a residual oil
  7. stirringthe mixture was stirred
  8. customto obtain a solution
  9. waitkept at room temperature overnight
  10. customto afford a suspension, which
  11. stirringwas stirred at ambient temperature for 30 minutes
  12. filtrationThe thus formed solid was collected by filtration
  13. washwashed with diethyl ether (2×5 ml)
  14. customdried
  15. customto afford

Sources & evidence

ORD record
ord-5a38da79bdd14a0d91e45795b0f2c13e
Source dataset
uspto-grants-2012_10
Patent number
US08293912B2

Reaction notes

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