Formaldehyde → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)propanoate

To a solution of ethyl 3-cyclopropyl-3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)amino)methyl)phenyl)propanoate (203 mg), formaldehyde solution (88 μL) and acetic acid (67 μL) in acetonitrile (3.9 mL) was added sodium triacetoxyborohydride (125 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated sodium hydrogen carbonate solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (148 mg) as a colorless transparent oil.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe extract was washed with saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent was evaporated under reduced pressure
5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD-Eintrag

ord-27b007be0acd46bc8308b76316fa3da2

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09382188B2