An approach for the diastereoselective synthesis of (<scp><i>R</i></scp>)‐(+)‐methyl pipecolate and (+)‐dextro‐erythrophacetoperane from (<scp><i>S</i></scp>)‐(−)‐methylbenzylamine-Reference-Cited by-同舟云学术

An approach for the diastereoselective synthesis of (R)‐(+)‐methyl pipecolate and (+)‐dextro‐erythrophacetoperane from (S)‐(−)‐methylbenzylamine

Published:2024-07-23 Issue: Volume: Page:
ISSN:0022-152X
Container-title:Journal of Heterocyclic Chemistry
language:en
Short-container-title:Journal of Heterocyclic Chem

Author:

Aguilar‐Aguilar Alan¹,Carrasco‐Carballo Alan²,Gnecco Dino¹,Rodríguez‐Matsui Hisami¹,Aparicio‐Solano David¹,Terán Joel L.¹

Affiliation:

1. Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC9, Complejo de Ciencias Puebla Mexico

2. Laboratorio de Elucidación y Síntesis en Química Orgánica, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla Puebla Mexico

Abstract

AbstractA diastereoselective synthesis for the preparation of (R)‐methyl pipecolate and dextro‐erythrophacetoperane, analogs of methylphenidate, drugs used to treat attention deficit hyperactivity disorder, is reported. The key steps involve a high diastereoselective ring‐closing reaction via enolate formation and a diastereoselective ketone reduction reaction. The total synthesis of these valuable drugs could be obtained in only 5 and 8 steps, respectively, starting from (S)‐(−)‐methyl benzylamine.

Funder

CONACYT

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.4878

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