Sodium Carbonate → Salsolidine

HRID 634960Notes

Reaction equation

HRID 634960 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH3:15])=[N:8][C:7](O)=[C:6]2O.C(N(CC)CC)C.C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>[Ru].C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C@H:9]([CH3:15])[NH:8][CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11084032Triethylammonium formateHCID 178486678HCID 178486678, compound

Product 1

HCID 164752SalsolidineYield 99%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 6342AcetonitrileSolvent

Procedure

6,7-Dimethoxy-l-methyl-3,4-dihydroxyisoquinoline (Table 6-2a)(1.03 g, 5 mmol) and a ruthenium catalyst (Table 7)(R, R)-1a (16 mg, 0.025 mmol) were dissolved in acetonitrile (10 ml), followed by addition of a mixture of formic acid-triethylamine (5:2), for agitation at 28° C. for 3 hours. To the reaction mixture was added an aqueous sodium carbonate solution to extract the product in ethyl acetate. After evaporation of the solvent, 1H-NMR(CDCl3) of the resulting product was measured to calculate the conversion. Then, the product was purified by silica gel chromatography, to determine the optical purity and absolute configuration of the resulting optically active amine by HPLC or GLC. As collectively shown in Table 8, (S)-6,7-dimethoxy-l-methyl-1,2,3,4-tetrahydroisoquinoline (1.02 g, yield of 99%, 96% ee) was obtained.

Workup

  1. extractionto extract the product in ethyl acetate
  2. customAfter evaporation of the solvent, 1H-NMR(CDCl3) of the resulting product
  3. customThen, the product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3b6cec76e2654b5eb9416632b602cda5
Source dataset
uspto-grants-2001_02
Patent number
US06184381B2

Reaction notes

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