[Synthesis isomeric 4-prolylamines and 4,4'-diprolylamines].
Starting from the previously described tert-butyl esters of 4-epimeric N-benzyloxycarbonyl-4-hydroxyprolines and N-benzyloxycarbonyl-4-trans- and 4-cis-trifluoroacetamidoproline tert-butyl esters, the corresponding un-protected 4-aminoprolines and a number of their partially protected derivatives were synthesized via the intermediate 4-O-mesyl and 4-azide derivatives. The reductive amination of N-benzyloxycarbonyl-4-oxoproline tert-butyl ester with ammonium acetate led to N-benzyloxycarbonyl-4-cis-4'-cis- and 4-cis-4'-trans-diprolinylamines. The 1H NMR and CD spectra of the synthesized compounds are described.
Elin
E A
EA
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, GSP-7 Moscow, 117871 Russia.
Onoprienko
V V
VV
Kudelina
I A
IA
Miroshnikov
A I
AI
D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C441108:4,4'-diprolylamine; C012179:1-aminoproline; D011392:Proline