Abstract
The reaction of tert-butyl 4-oxopiperidine-1-carboxylate dimethylhydrazone with BuLi and further with iodides of protected alcohols ICH2(CH2) n OSiMe2(t-Bu) (n = 1–4) led to the formation of the corresponding tert-butyl 3-{[tert-butyl(dimethyl)silyl]alkyl}-4-oxopiperidine-1-carboxylates that under the treatment with triethylsilane in the presence of anhydrous BiBr3 underwent cyclization with a high stereoselectivity into cis-isomers of N-Boc piperidine derivatives [3,2-c]-fused with oxygen heterocycles. The latter at the treatment with anhydrous HCl eliminate the Boc group affording hydrochlorides of stereochemically homogeneous N-unsubstituted fused bicyclic systems.
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Original Russian Text © A.I. Moskalenko, V.I. Boev, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 8, pp. 1136–1141.
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Moskalenko, A.I., Boev, V.I. Stereoselective synthesis of piperidine derivatives [3,2-c]-fused with oxygen heterocycles. Russ J Org Chem 50, 1117–1123 (2014). https://doi.org/10.1134/S1070428014080089
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DOI: https://doi.org/10.1134/S1070428014080089