A concise and efficient synthesis of vildagliptin

Michele Castaldi; Marco Baratella; Ivan G. Menegotto; Graziano Castaldi; Giovanni B. Giovenzana

doi:10.1016/j.tetlet.2017.07.062

A concise and efficient synthesis of vildagliptin

Michele Castaldi
, Marco Baratella
, Ivan G. Menegotto
, Graziano Castaldi
, Giovanni B. Giovenzana

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

An original synthesis of vildagliptin ((S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carbonitrile), a powerful DPP-4 inhibitor, was developed. Vildagliptin was assembled from 3-amino-1-adamantanol, glyoxylic acid and L-prolinamide in a 4-step reaction sequence with the isolation of only two intermediates. The procedure is competitive with existing protocols, leading to vildagliptin in 63% overall yield.

Original language	English
Pages (from-to)	3426-3428
Number of pages	3
Journal	Tetrahedron Letters
Volume	58
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2017.07.062
Publication status	Published - 2017

Keywords

3-Amino-1-adamantanol
DPP-4 inhibitors
L-Prolinamide
Vildagliptin

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10.1016/j.tetlet.2017.07.062

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title = "A concise and efficient synthesis of vildagliptin",

abstract = "An original synthesis of vildagliptin ((S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carbonitrile), a powerful DPP-4 inhibitor, was developed. Vildagliptin was assembled from 3-amino-1-adamantanol, glyoxylic acid and L-prolinamide in a 4-step reaction sequence with the isolation of only two intermediates. The procedure is competitive with existing protocols, leading to vildagliptin in 63\% overall yield.",

keywords = "3-Amino-1-adamantanol, DPP-4 inhibitors, L-Prolinamide, Vildagliptin",

author = "Michele Castaldi and Marco Baratella and Menegotto, \{Ivan G.\} and Graziano Castaldi and Giovenzana, \{Giovanni B.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tetlet.2017.07.062",

language = "English",

volume = "58",

pages = "3426--3428",

journal = "Tetrahedron Letters",

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T1 - A concise and efficient synthesis of vildagliptin

AU - Castaldi, Michele

AU - Baratella, Marco

AU - Menegotto, Ivan G.

AU - Castaldi, Graziano

AU - Giovenzana, Giovanni B.

PY - 2017

Y1 - 2017

N2 - An original synthesis of vildagliptin ((S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carbonitrile), a powerful DPP-4 inhibitor, was developed. Vildagliptin was assembled from 3-amino-1-adamantanol, glyoxylic acid and L-prolinamide in a 4-step reaction sequence with the isolation of only two intermediates. The procedure is competitive with existing protocols, leading to vildagliptin in 63% overall yield.

AB - An original synthesis of vildagliptin ((S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carbonitrile), a powerful DPP-4 inhibitor, was developed. Vildagliptin was assembled from 3-amino-1-adamantanol, glyoxylic acid and L-prolinamide in a 4-step reaction sequence with the isolation of only two intermediates. The procedure is competitive with existing protocols, leading to vildagliptin in 63% overall yield.

KW - 3-Amino-1-adamantanol

KW - DPP-4 inhibitors

KW - L-Prolinamide

KW - Vildagliptin

UR - https://www.scopus.com/pages/publications/85025470989

U2 - 10.1016/j.tetlet.2017.07.062

DO - 10.1016/j.tetlet.2017.07.062

M3 - Article

SN - 0040-4039

VL - 58

SP - 3426

EP - 3428

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

A concise and efficient synthesis of vildagliptin

Abstract

Keywords

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