Sodium Hydroxide → (-)-2-(Aminoethylthio)methyl-3-carboethoxy-5-carbomethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine fumarate

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Reaction Steps

A mixture of (-)-2-[(1,4,5,6-tetrahydropyrimidin-2-yl)thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (g 2), hexadecyltributyl phosphonium bromide (mg 180), 2-bromoethylaminehydrobromide (mg 900), NaOH (35%, ml 8) and benzene is stirred for 40 minutes at room temperature. After the usual work-up, an oily residue is obtained that is dissolved in ethyl acetate and treated with fumaric acid to give 1.9 g of (-)-2-(aminoethylthio)methyl-3-carboethoxy-5-carbomethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine fumarate, m.p. 104°-110° C. [α]D =-11 (C=4 in MeOH).

Provenance & Evidence