Boron tribromide → HCID 86610735, compound

To a solution of 6-methoxy-1-(R)-(2-bromoethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (390 mg, 1.07 mmol) obtained in step (c) of Example 190 in dichloromethane (5 ml) was added 1M solution of boron tribromide in dichloromethane (2.14 ml, 2.14 mmol) gradually at −78° C. with stirring. The resulting mixture was further stirred at −78° C., and after confirming the disappearance of the starting material by thin layer chromatography, saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and after raising the temperature to ambient temperature, the resulting mixture was extracted with ethyl acetate. The extract was washed successively with dilute hydrochloric acid and 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 (280 mg, yield: 75%) as a colorless oil.

1. stirringThe resulting mixture was further stirred at −78° C.
2. additionwas added to the reaction mixture
3. extractionthe resulting mixture was extracted with ethyl acetate
4. washThe extract was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated in vacuo
7. customThe residue obtained
8. customwas purified by chromatography on a silica gel column

ORD record

ord-65d431d7209b45498ff11f66c2e891a5

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504393B2