Methanol → Methyl 4-({(5-methoxy-5-oxopentyl)[2-(5-fluoro-2-hydroxyphenyl)ethyl]amino}methyl)benzoate

Temperature

0 °C

2.6 g (5.84 mmol) of methyl 4-({(5-ethoxy-5-oxopentyl)[2-(5-fluoro-2-methoxy-phenyl)ethyl]amino}methyl)benzoate are dissolved in 50 ml of dichloromethane, the mixture is cooled to 0° C., and 19.3 ml (19.3 mmol) of a 1N solution of boron tribromide in dichloromethane are added dropwise. The solution is stirred at 0° C. for one hour. 50 ml of methanol are slowly added dropwise at 0° C., and the reaction mixture is heated at reflux overnight. The mixture is cooled and the solvents are evaporated under reduced pressure. The residue is taken up in ethyl acetate and washed with sodium carbonate, the aqueous phase is extracted three times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue is chromatographed over silica gel (cyclohexane:ethyl acetate (5:1) to ethyl acetate: methanol (9:1)).

1. temperaturethe reaction mixture is heated
2. temperatureat reflux overnight
3. temperatureThe mixture is cooled
4. customthe solvents are evaporated under reduced pressure
5. washwashed with sodium carbonate
6. extractionthe aqueous phase is extracted three times with ethyl acetate
7. washthe combined organic phases are washed with saturated sodium chloride solution
8. dry with materialdried over magnesium sulphate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue is chromatographed over silica gel (cyclohexane:ethyl acetate (5:1) to ethyl acetate: methanol (9:1))

ORD record

ord-526ea56d1ca64fa7802984b594b2d839

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517896B2