Synthesis
DOI: 10.1055/a-1526-7657
psp

Convenient Synthesis of (R)-3-[(tert-Butoxycarbonyl)amino]piperidine and (R)-3-[(tert-Butoxycarbonyl)amino]azepane

a  Institute of Inorganic Chemistry, Academy of Sciences of the Czech Republic, 25068 Řež, Czech Republic
b  Evonik Resource Efficiency GmbH, Rodenbacher Chaussee 4, 63457 Hanau, Germany
,
Oleg L. Tok
a  Institute of Inorganic Chemistry, Academy of Sciences of the Czech Republic, 25068 Řež, Czech Republic
› Author Affiliations


Abstract

(R)-3-[(tert-Butoxycarbonyl)amino]piperidine and (R)-3-[(tert-butoxycarbonyl)amino]azepane were prepared in two steps starting from d-ornithine and d-lysine, respectively. In the key step, N-Boc-protected 3-aminolactams were converted into imido esters by O-alkyl­ation and then hydrogenated to amines, under mild conditions (5 bar H2, room temperature) and without isolation, over a standard hydrogenation catalyst (5% Pt/C).

Supporting Information



Publication History

Received: 21 May 2021

Accepted: 10 June 2021

Publication Date:
10 June 2021 (online)

© 2021. Thieme. All rights reserved

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