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

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).

Key words

amides - amines - hydrogenation - heterogeneous catalysis - chirality

Publication History

Received: 21 May 2021

Accepted: 10 June 2021

Accepted Manuscript online:
10 June 2021

Article published online:
13 July 2021

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