Methyl iodide → HCID 86643175, compound

HRID 1808320Notes

Reaction equation

HRID 1808320 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][CH3:37])=[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:46]C>O.C(OCC)C>[I-:46].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C@:18]2([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[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 67538081HCID 67538081, compound

Product 1

HCID 86643175HCID 86643175, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

(1R)-1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methoxycarbonylethylisoquinoline oxalate (7.0 g, 0.0135 moles) was dissolved in water (50 ml) and aqueous sodium bicarbonate solution was added to produce a pH in the range of 9-10. Dichloromethane (100 ml) was added and the mixture was stirred for 15 minutes at that temperature. The upper organic layer was separated and the aqueous layer was extracted three times with dichloromethane (3×100 ml). The combined organic layer was dried over magnesium sulfate and washed with 10% sodium chloride solution. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to afford a residual oil. Iodomethane (30 ml, 0.482 moles) was added to the oily residue and the mixture was stirred to obtain a solution and kept at ambient temperature overnight. The reaction mixture was added to diethyl ether (100 ml) to afford a suspension. The suspension was stirred at ambient temperature for 30 minutes to afford a solid, which was collected by filtration, washed with diethyl ether (2×15 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-methoxycarbonylethyl-isoquinolinium iodide (5.9 g; 77% 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 (3×100 ml)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. washwashed with 10% sodium chloride solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto afford a residual oil
  9. stirringthe mixture was stirred
  10. customto obtain a solution
  11. waitkept at ambient temperature overnight
  12. customto afford a suspension
  13. stirringThe suspension was stirred at ambient temperature for 30 minutes
  14. customto afford a solid, which
  15. filtrationwas collected by filtration
  16. washwashed with diethyl ether (2×15 ml)
  17. customdried
  18. customto afford

Sources & evidence

ORD record
ord-0358450d686f4ccdb44c831ea54f6a29
Source dataset
uspto-grants-2013_01
Patent number
US08357807B2

Reaction notes

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