220058-24-2Relevant academic research and scientific papers
Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines-development of a phosphite-driven cyclodehydration
Huy, Peter H.,Westphal, Julia C.,Koskinen, Ari M.P.
supporting information, p. 369 - 383 (2014/03/21)
A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.
Efficient, stereodivergent access to 3-piperidinols by traceless P(OEt)3 cyclodehydration
Huy, Peter H.,Koskinen, Ari M. P.
, p. 5178 - 5181 (2013/11/06)
A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)3 as a substitute for PPh3 is developed.
Enantioselective ring expansion of prolinols: An efficient and short synthesis of 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids
Cochi, Anne,Burger, Benjamin,Navarro, Cristina,Pardo, Domingo Gomez,Cossy, Janine,Zhao, Yang,Cohen, Theodore
experimental part, p. 2157 - 2161 (2009/12/24)
A very short route to 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids is described. The approach uses two key steps: a one-pot reduction/Grignard addition sequence applied to alkyl proline esters and a ring expansion applied to the corresp
Stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidines, precursors of non-peptidic substance P antagonists
Calvez, Olivier,Langlois, Nicole
, p. 7099 - 7100 (2007/10/03)
(2S)-N-Boc-3-oxo-2-phenylpiperidine 5 and (2S,3S)-N-Boc-3-hydroxy-2- phenylpiperidine 6, known chiral building blocks for the synthesis of non- peptidic substance P antagonists, were prepared from erythro (2S)-N-benzyl 2- hydroxybenzylpyrrolidine derived from (S)-N-methoxy-N-methylpyroglutamide.
Enantioselective synthesis of 2,3-disubstituted piperidines from (S)- methylpyroglutamate
Calvez, Olivier,Chiaroni, Angele,Langlois, Nicole
, p. 9447 - 9450 (2007/10/03)
N-methoxy-N-methylamide derived from (S)-methylpyroglutamate was prepared in good yield and allowed the addition of Grignard reagents. Erythro (2S)-1-benzyl-2-hydroxybenzyl pyrrolidine obtained by this way was converted into (2S,3R)-1-benzyl-3-hydroxy-2-phenylpiperidine and its chloro analog.
