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

0544130 - ÚACH 2022 RIV DE eng J - Journal Article
Kadyrov, Renat - Tok, Oleg L.
Convenient Synthesis of (R)-3-[(tert-Butoxycarbonyl)amino]-piperidine and (R)-3-[(tertButoxycarbonyl)amino]azepane.
Synthesis. Roč. 53, č. 19 (2021), s. 3573-3577. ISSN 0039-7881. E-ISSN 1437-210X
Institutional support: RVO:61388980
Keywords : alpha-amino-acids * conformationally constrained analogs * pharmacophore-based molecules * scalable biocatalytic route * integrin-alpha(v)beta(3) antagonists * delta-lactams
OECD category: Inorganic and nuclear chemistry
Impact factor: 3.019, year: 2021
Method of publishing: Limited access
https://doi.org/10.1055/a-1526-7657

(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 H-2, room temperature) and without isolation, over a standard hydrogenation catalyst (5% Pt/C).
Permanent Link: http://hdl.handle.net/11104/0322720