Journal of the Chemical Society. Perkin transactions I p. 2925 - 2932 (1996)
Update date:2022-08-04
Topics:
Perrio-Huard, Cecile
Ducandas, Christophe
Lasne, Marie Claire
Moreau, Bernard
Several routes to the synthesis of the polyamines 2a and 2b required for the preparation of the muscarinic antagonists AF-DX 384 1a and its perhydroazepine isomer 1b respectively have been developed and compared. Piperidine 2a has been obtained in 4 steps in 13-15% overall yield from 2-(chloromethyl)-pyridine 3. The perhydroazepine 2b has been prepared in 4 steps in 49% overall yield from 3-aminolactam 7. Transformations of piperidinemethanol 11 afford exclusively compound 2a (5 steps, 17-20% overall yield), via the N-tosylpiperidine 12, but lead to a 1:1 mixture of isomers 2a and 2b (4 steps, 15-20% overall yield for compounds 2a and 2b) via the N-(cyanomethyl)piperidine 15. Limitations to the ring enlargement of piperidine derivatives as a function of the heterocyclic nitrogen substituent are defined.
View MoreSINO Industries Company Limited
Contact:86-29-85369724
Address:No.111, Jiefang Road, Xi’an, China
CGeneTech (Suzhou, China) Co., Ltd.
Contact:+86-512-62956962
Address:Room 101,Bld C11,218 Xinghu Rd.,Suzhou industrial Park
Contact:732.938.2777
Address:5012 Industrial Road Farmingdale, NJ 07727
Taizhou volsen chemical Co., Ltd
website:http://www.volsenchem.com
Contact:+86-576-88869393
Address:Jiaojiang District, Taizhou, Zhejiang, China.
QINGDAO TAOSIGN INTERNATIONAL TRADE CO.,LIMITED
Contact:+86-0532-82683616
Address:RM1402, Doublestar Seacoase 7#, No. 5 Guizhou Road, Qingdao, Shandong, China
Doi:10.1016/S0022-328X(00)82214-7
(1964)Doi:10.1021/jo961955w
(1997)Doi:10.1021/om9609168
(1997)Doi:10.1016/S0040-4039(96)02352-0
(1997)Doi:10.1039/a601642a
(1997)Doi:10.1021/jm970685m
(1998)