A convenient route to 1-benzyl 3-aniinopyrrolidine and 3-aminopiperidine

Authors
Jean, L Baglin, I Rouden, J Maddaluno, J Lasne, MC
Citation
L. Jean et al., A convenient route to 1-benzyl 3-aniinopyrrolidine and 3-aminopiperidine, TETRAHEDR L, 42(33), 2001, pp. 5645-5649
Citations number
49
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
33
Year of publication
2001
Pages
5645 - 5649
Database
ISI
SICI code
0040-4039(20010813)42:33<5645:ACRT13>2.0.ZU;2-F
Abstract
1-Benzyl 3-aminopyrrolidine 1 and 1-benzyl 3-aminopiperidine 2 were prepare d rapidly mainly in aqueous conditions in 55 and 75%, yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The key step involved the Curtius rearrangement mediat ed by sodium nitrite and trifluoroacetic acid of the appropriate acylhydraz ides. All the reactions (except LAH reductions) were performed in water. (C ) 2001 Elsevier Science Ltd. All rights reserved.