Development of a catalytic tributyltin hydride cyclisation process

Citation
Rp. Attrill et al., Development of a catalytic tributyltin hydride cyclisation process, ORG PROC R, 4(2), 2000, pp. 98-101
Citations number
5
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC PROCESS RESEARCH & DEVELOPMENT
ISSN journal
1083-6160 → ACNP
Volume
4
Issue
2
Year of publication
2000
Pages
98 - 101
Database
ISI
SICI code
1083-6160(200003/04)4:2<98:DOACTH>2.0.ZU;2-U
Abstract
The development of a pilot plant process to prepare the spirocyclic piperid ine (2) from the tetrahydropyridine (4) via a radical cyclisation reaction is described. The pilot plant process involves the use of a catalytic amoun t of tributyltin hydride (0.14 equiv) generated in situ by the reaction of tributyltin chloride with sodium borohydride (1.1 equiv) in 2-propanol/etha nol containing azo-bis(isobutyronitrile) (AIBN). Initial laboratory conditi ons are described as well as the changes made on transfer to the pilot plan t. Measurement of the levels of residual amounts of tin in the batches of ( 2) produced are reported.