(-)-(R)-N-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl) methyl-N-phenylmethyl-N'-(2-pyrimidinyl)-1,2-ethanediamine → (-)-(R)-N-[(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine

Participants

Reaction Steps

A mixture of 8.4 g of (-)-(R)-N-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl) methyl-N-phenylmethyl-N'-(2-pyrimidinyl)-1,2-ethanediamine and 150 ml methanol was hydrogenated in the presence of 2 g of palladium-on-charcoal catalyst (10%). After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 90:10). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.5 g (55.1%) of (-)-(R)-N-[(6-fluoro-3,4-dihydro-2H-1-benzopyran-2yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine; mp. 103.2° C. [α]D 20 =-76.58° (conc.=1% in CH3OH) (comp. 46).

Provenance & Evidence