✦ LIBER ✦

Remarkable switch of regioselectivity in epoxide ring opening of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane with amines: practical synthesis of trans-4-amino-3-hydroxypiperidines and trans-3-amino-4-hydroxypiperidines

✍ Scribed by Osamu Tokuda; Toshiaki Aikawa; Tetsuya Ikemoto; Isao Kurimoto

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 490 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.03.061

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✦ Synopsis

A simple and highly C3 selective ring-opening method for 3,4-epoxypiperidines has been developed. We also describe a practical improvement of the C4 selective ring-opening method using the same N-alkyl substituted 3,4-epoxypiperidines. This method provides access to pharmaceutically relevant trans-3amino-4-hydroxypiperidines and trans-4-amino-3-hydroxypiperidines with simple procedures.