New general synthesis of α-alkoxyketones via α′-alkylation, α-alkylation and α,α′-dialkylation of α-alkoxyketimines
作者:Filip Colpaert、Sven Mangelinckx、Maria Teresa Rocchetti、Norbert De Kimpe
DOI:10.1039/c0ob00662a
日期:——
important intermediates in organic synthesis and flavor compounds in food chemistry, were synthesized by deprotonation of N-(1-alkoxy-2-propylidene)isopropylamine, prepared by condensation of the corresponding α-alkoxyacetone with isopropylamine, and subsequent reaction of the corresponding 1-azaallylic anions with alkyl halides to afford α′-alkylated, α-alkylated and α,α′-dialkylated ketimines. Hydrolysis
Cis and trans 3-amino-4-hydroxypyrrolidines and derivatives thereof are disclosed having the formula: ##STR1## wherein R.sub.1 is hydrogen, loweralkyl or phenylcarbonyl; R.sub.2 is hydrogen, loweralkyl, lowercycloalkyl, phenyl or phenylloweralkyl; R.sub.3 is hydrogen, loweralkyl, phenylloweralkyl, phenylcarbonyl, diphenylmethyl, 5-yl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene or naphthylcarbonyl; R.sub.4 is hydrogen, loweralkyl, phenylloweralkyl or lowercycloalkyl; phenyl is optionally substituted and acid addition salts thereof. The compounds have antidepressant activity and methods and pharmaceutical compositions for use thereof are disclosed.