6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → HCID 18403866, compound

HRID 1017681Notes

Reaction equation

HRID 1017681 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][C:7]=1[O:14][CH3:15])=[O:4].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[CH2:25][NH:24][CH2:23][CH2:22]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][N:2]([CH3:16])[C:3]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][N:24]2[CH2:23][CH2:22][C:21]3[C:26](=[CH:27][C:28]([O:29][CH3:30])=[C:19]([O:18][CH3:17])[CH:20]=3)[CH2:25]2)=[CH:8][C:7]=1[O:14][CH3:15])=[O:4]

Participants

5

Reactant 3

HCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 5049666Sodium triacetoxyborohydrideHCID 18403787HCID 18403787, compound

Product 1

HCID 18403866HCID 18403866, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(dimethylaminocarbonyloxy)-3-(methoxy)benzaldehyde (1.02 g) in 1,2-dichloroethane (16 ml) was added 6,7-dimethoxytetrahydroisoquinoline(0.97 g) and sodium triacetoxyborohydride (1.35 g), with stirring. The mixture was stirred at ambient temperature for 1 hr, poured onto ice/sodium carbonate solution and extracted with ethyl acetate. The extracts were washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash column chromatographed (silica gel), eluting with dichloromethane, 1% and 2% methanol dichloromethane. The appropriate fractions were collected and concentrated to give 0.92 g (50.3%/o) of product. Recrystallization from ethyl acetate gave the analytical sample, mp 126-128° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 1 hr
  2. additionpoured onto ice/sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water, saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. dissolutionThe residue was dissolved in dichloromethane
  9. customflash column chromatographed (silica gel)
  10. washeluting with dichloromethane, 1% and 2% methanol dichloromethane
  11. customThe appropriate fractions were collected
  12. concentrationconcentrated
  13. customto give 0.92 g (50.3%/o) of product
  14. customRecrystallization from ethyl acetate
  15. customgave the analytical sample, mp 126-128° C.

Sources & evidence

ORD record
ord-45e12a0e70a741ddb857c0b2b4c33920
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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