PURPOSE: To stereospecifically produce a (R)-6-amino-1-alkyl-4-benzylhexahydro-1 H-1,4-diazepine derivative useful as a precursor of a synthetic intermediate for a compound having strong antiemetic action by using two kinds of enantiomers as starting compounds and treating with a specific reducing agent to effect the cyclization of the compounds.
CONSTITUTION: The objective (R)-6-amino-1-alkyl-4-benzylhexahydro-1H-1,4- diazepine derivative of formula III can be produced either by reacting a compound of formula I (R1 is an alkyl; R2 is H, F, Cl, Br, methyl or methoxy; X1 is an amino-protecting group) or its acid addition salt with glyoxal under reducing condition or by treating a compound of formula II (Y is an esterified carboxyl or cyano) with a reducing agent for formylation and then treating with a reducing agent capable of reducing immonium salt. The compound of formula III is useful as a precursor of a synthetic intermediate for a compound exhibiting antiemetic action by strong serotonin 3(5-HT3) receptor antagonistic action and its relating compounds.
MORIE TOSHIYA
HARADA HIROSHI
HIROKAWA YOSHIMI
YOSHIDA TOYOKICHI
SUZUKI TOSHIBUMI
