Hydrochloric Acid → 6-benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester

HRID 1833138Notes

Reaction equation

HRID 1833138 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[N:5]([CH:12]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:22]([O:34][CH3:35])[CH:21]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][CH:7](OC)OC)[CH3:2].Cl.[OH-].[Na+].[C:40](OCC)(=[O:42])C.CCCCCC>CC(C)=O>[CH2:1]([O:3][C:4]([N:5]1[CH:6]=[CH:7][C:25]2[C:20](=[CH:21][C:22]([O:34][CH3:35])=[C:23]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:24]=2)[CH:12]1[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([O:42][CH3:40])[CH:19]=1)=[O:36])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 69550811[1-(4-Benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester

Product 1

HCID 210349386-benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of [1-(4-benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester (100 mg, 0.19 mmol) in acetone (5 mL) was added 6N hydrochloric acid (1 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 hrs and neutralized by addition of 6N aqueous sodium hydroxide solution. The solvent was evaporated and the aqueous phase was extracted with dichloromethane (3×25 μL). The combined extracts were washed with saturated aqueous sodium chloride solution (10 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane) afforded 6-benzyloxy-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (60 g, 85% yield) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. extractionthe aqueous phase was extracted with dichloromethane (3×25 μL)
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution (10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5457038e839c49db940ba13df8380cd4
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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