Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine

Nucleophilic substitution of the halogen atom in dimethyl ( S )-4-bromoglutamate followed by removal of the protecting groups and closure of a lactam ring afforded (2 S ,4 S )-4-(indolin-1-yl)-5-oxoproline. The indoline fragment was oxidized into the indole fragment to give (2 S ,4 S )-4-(indol-1-yl...

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Published inRussian chemical bulletin Vol. 60; no. 5; pp. 873 - 881
Main Authors Vigorov, A. Yu, Nizova, I. A., Shalunova, K. E., Grishakov, A. N., Sadretdinova, L. Sh, Ganebnykh, I. N., Ezhikova, M. A., Kodess, M. I., Krasnov, V. P.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.05.2011
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
glutamic acid
proline
5-oxoproline
4-aminoproline
indole
prolinol
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Summary:Nucleophilic substitution of the halogen atom in dimethyl ( S )-4-bromoglutamate followed by removal of the protecting groups and closure of a lactam ring afforded (2 S ,4 S )-4-(indolin-1-yl)-5-oxoproline. The indoline fragment was oxidized into the indole fragment to give (2 S ,4 S )-4-(indol-1-yl)-5-oxoproline; reduction of the carbonyl groups with BH3 yielded (2 S ,4 S )-4-(indol-1-yl)prolines and (2 S ,4 S )-2-hydroxymethyl-4-(indol-1-yl)pyrrolidines. Reduction of (2 S ,4 S )-4-arylamino-5-oxoprolines with BH3 to the corresponding (2 S ,4 S )-4-arylaminoprolines and (2 S ,4 S )-4-arylamino-2-hydroxymethylpyrrolidines was studied.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-011-0137-4