1,2-Diphenylethylamine → (-)-2-(2-Hydroxyphenyl)-5-pyrrolinecarboxylic acid (-)-1,2-diphenylethylamine salt

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Reaction Steps

35.8 g of (±)-2-(2-hydroxyphenyl)-5-pyrrolinecarboxylic acid is reacted with 34.5 g of (-)-1,2-diphenylethylamine to give the diastereoisomer salt. The salt is fractionally recrystallized from ethanol to give (-)-2-(2-hydroxyphenyl)-5-pyrrolinecarboxylic acid (-)-1,2-diphenylethylamine salt, yield 20.0 g (57%), mp. 193°-194° C., [α]D26 -90.0° (c=1.0, methanol). The residual salt in the filtrate is fractionally recrystallized from chloroform to give (+)-2-(2-hydroxyphenyl)-5-pyrrolinecarboxylic acid (-)-1,2-diphenylethylamine salt, yield 18.0 g (51%), mp. 138°-140° C., [α]D26 -20.3° (c=1.2, methanol).

Provenance & Evidence