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Synthesis of 3‐(2‐Aminoethyl)pyrrole Derivatives
Author(s) -
Demopoulos Vassilis J.
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250249
Subject(s) - chemistry , pyrrole , aluminum hydride , acetaldehyde , hydrolysis , reductive amination , substituent , medicinal chemistry , yield (engineering) , lithium (medication) , amination , hydride , organic chemistry , catalysis , metal , ethanol , medicine , materials science , methoxide , metallurgy , endocrinology
3‐(2‐Di‐ n ‐propylaminoethyl)pyrrole (1a) was prepared in good yield by reduction of pyrrole‐3‐( N,N ‐di‐ n ‐propylglyoxamide) (9) with lithium aluminum hydride. 3‐(2‐Di‐ n ‐propylaminoethyl)‐5‐acetylpyrrole (1b) was prepared by first acetylation of 1‐ p ‐toluenesulfonyl‐3‐(2‐di‐ n ‐propylaminoethyl)pyrrole (6) followed by hydrolysis of the p ‐toluenesulfonyl substituent. The starting material 6 was prepared by homologation of 1‐( p ‐toluenesulfonyl)pyrrole‐3‐carboxaldehyde (3) to the corresponding acetaldehyde followed by reductive amination of the latter.