* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
13
To a solution of tert-butyl l-(3-bromophenyl)ethylcarbamate (300 mg, 1 mmol) in methanol (10 mL) was added [l,l'-bis(diphenyl-phosphino)ferrocene]palladium [II]chloride, 1 : 1 complex with dichloromethane (146 mg, 0.2 mmol) then triethylamine (0.28 mL, 2 mmol). The mixture was evacuated and backfilled with carbon monoxide four times and was then heated to reflux and stirred under an atmosphere of carbon monoxide for 17 hours. After this time the mixture was filtered through Celite to give a brown solid which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give methyl 3-{ l-[(tert-butoxycarbonyl)amino]ethyl}benzoate (210 mg, 75%) as a white solid.
Stage #1: methyl 3-{1-[(tert-butoxycarbonyl)amino]ethyl}benzoate With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h;
Stage #2: With ammonia; water
13
A solution of methyl 3-{l-[(tert-butoxycarbonyl)amino]ethyl}benzoate (200 mg, 0.72 mmol) in 20% trifluoroacetic acid in dichloromethane (10 mL) was stirred at room temperature for 1.5 hours. After this time the mixture was concentrated under reduced pressure and the residue was dissolved in water and basified to pH 11 with aqueous ammonia. The mixture was extracted with ethyl acetate (2 x 15 mL) and the extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give methyl 3-(l-aminoethyl)benzoate (130 mg, 100%) as a pale yellow oil.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
100K+ Compounds
Competitive Price
1-2 Day Shipping
