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

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.

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

ORD record

ord-5457038e839c49db940ba13df8380cd4

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067529B2