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Preparation of ( R )‐3‐aminopiperidine by resolution with optically active cyclic phosphoric acids
Author(s) -
Sun Yujuan,
Hu Beibei,
Jing Yongshuai,
Wu Jialiang,
Zhou Maochao,
Chen Meng,
Hao Feifei,
Zhang Chen,
Sun Fengxia
Publication year - 2021
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23312
Subject(s) - chemistry , diastereomer , resolution (logic) , combinatorial chemistry , yield (engineering) , optically active , nanotechnology , stereochemistry , organic chemistry , programming language , materials science , computer science , metallurgy
( R )‐3‐aminopiperidine (( R )‐APD), a key intermediate for alogliptin, trelagliptin, and linagliptin, was successfully resolved from racemic 3‐aminopiperidine with an enantiomerically pure resolving agent, namely, ( R )‐4‐(2‐chlohydroxy‐1.3.2‐dioxaphosphorinane 2‐oxide (( R )‐CPA), via diastereomeric salt formation. By this resolution approach, ( R )‐3‐aminopiperidine was obtained in 99.5% yield with 99.6% e.e .
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