138566-17-3Relevant articles and documents
A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics
Yang, Yuyan,Li, Hua,You, Zhonglin,Zhang, Xingxian
, p. 3084 - 3089 (2021)
A novel and enantioselective synthesis of (S)-2-pipecolic acid (5) has been achieved from Oppolzer’s sultam (1) and ethyl N-(diphenylmethylene)glycinate (2) as readily available starting materials. The highly stereoselective alkylation of chiral glycine intermediate (3) with 1,4-dibromobutane afforded the key backbone of (S)-2-pipecolic acid (5) in one-step that was utilized into the preparation of the local anesthetics mepivacaine, ropivacaine and bupivacaine.
Preparation method of (S)-2-piperidinecarboxylic acid
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Paragraph 0061-0076, (2020/12/09)
A preparation method of (S)-2-piperidinecarboxylic acid comprises the following steps: under the catalysis of Lewis acid, carrying out condensation reaction on L-camphor sulfonamide (I) and diphenyl imine ester (II) to generate a compound (III); enabling the compound (III) and the compound (IV) to be subjected to asymmetric alkylation under the action of strong base, imine hydrolysis under an acidic condition and intramolecular cyclization by a one-pot method to obtain a compound (V); and removing a chiral auxiliary group from the compound (V) under an alkaline condition to obtain a target compound (S)-2-piperidinecarboxylic acid (TM), wherein the formulas (I), (II), (III), (IV) and (V) are described in the specification. The target product can be obtained through three steps in total, themethod has the advantages of cheap and easily available raw materials, short route, high yield, good stereoselectivity and the like, and the (S)-2-piperidinecarboxylic acid is an important chiral intermediate of multiple medicines at present and has a good market prospect.
Asymmetric synthesis of L-diphenylalanine and L-9-fluorenylglycine via room temperature alkylations of a sultam-derived glycine imine
Josien,Martin Chassaing
, p. 6547 - 6550 (2007/10/02)
L-diphenylalanine and L-9-fluorenylglycine were prepared from a sultam-derived glycine imine 3 via room temperature-asymmetric-alkylation/hydrolysis/mild-sultam-clivage. The L-configuration was ascertained using an X-ray analysis of the alkylation product 4b.
