Water → HCID 86610732, compound

To a solution of 6-methoxy-1-(R)-(2-t-butyldimethylsilyloxyethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (1.14 g, 2.73 mmol) obtained in step (a) of Example 190 in acetonitrile (10 ml) was added dropwise 48% solution of hydrofluoric acid in water (0.5 ml, 13.67 mmol) gradually with stirring under cooling in a water bath. The resulting mixture was further stirred at room temperature, and after confirming the disappearance of the starting material by thin layer chromatography, saturated aqueous sodium hydrogen carbonate solution was added with stirring, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1) as the eluent to afford the title compound (0.65 g, yield: 79%) as a colorless oil.

1. temperatureunder cooling in a water bath
2. stirringThe resulting mixture was further stirred at room temperature
3. additionwas added
4. stirringwith stirring
5. extractionthe resulting mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated aqueous sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. customevaporated in vacuo
9. customThe residue obtained
10. customwas purified by chromatography on a silica gel column

ORD record

ord-810f16b7ef66497bb4aef6c797da3d2b

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504393B2