Methanol → HCID 91576878, compound

HRID 1944228Notes

Reaction equation

HRID 1944228 reaction equation
CO.[C:3](Cl)(=[O:5])C.C(Cl)Cl.[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH:24]=[N:23][CH:22]=[CH:21]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1.C(OCC)(=O)C.CO>[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][NH:23][CH2:22][CH:21]2[O:5][CH3:3])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 427881HCID 427881, compound

Product 1

HCID 91576878HCID 91576878, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

F11 (5.4 g, 13.5 mmol) was stirred in THF (80 mL) and methanol (10 mL) and cooled to 0° C. before acetyl chloride (5.8 mL, 80 mmol) was added drop wise. The solution was stirred at rt o/n, After addition of DCM (100 mL), the organic layer was successively washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated to afford 4.2 g of a crude dark yellow solid. Column chromatography (petroleum ether/ethyl acetate 9/1 to 0/1 then ethyl acetate/methanol 1/0 to 10/1) afforded 1.8 g (45%) of 6-Benzyloxy-4,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline F12 and 6-benzyloxy-7-methoxyisoquinoline F13 (400 mg, 11%);

Workup

  1. additionwas added drop wise
  2. washthe organic layer was successively washed with saturated aqueous NaHCO3, water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 4.2 g of a crude dark yellow solid

Sources & evidence

ORD record
ord-efeced4415244afcb1ce3f969e17dd71
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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