3105-95-1Relevant articles and documents
One-Step Synthesis of L-Piperidine-2-carboxylic Acid
Kisfaludy, Lajos,Korenczki, Ferenc,Katho, Agnes
, p. 163 (1982)
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Enzymatic synthesis of L-pipecolic acid by Δ1-piperideine- 2-carboxylate reductase from Pseudomonas putida
Muramatsu, Hisashi,Mihara, Hisaaki,Yasuda, Mari,Ueda, Makoto,Kurihara, Tatsuo,Esaki, Nobuyoshi
, p. 2296 - 2298 (2006)
L-Pipecolic acid is a chiral pharmaceutical intermediate. An enzymatic system for the synthesis of L-pipecolic acid from L-lysine by commercial L-lysine α-oxidase from Trichoderma viride and an extract of recombinant Escherichia coli cells coexpressing Δ1-piperideine-2- carboxylate reductase from Pseudomonas putida and glucose dehydrogenase from Bacillus subtilis is described. A laboratory-scale process provided 27 g/l of L-pipecolic acid in 99.7% e.e.
Preparation method of caine drug intermediate (S)-2-piperidinecarboxylic acid
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, (2021/06/22)
The invention discloses a preparation method of a caine drug intermediate (S)-2-piperidinecarboxylic acid. The preparation method specifically comprises the following steps of a) carrying out a one-pot reaction on 5-chlorovaleraldehyde, L-phenylglycinol and trimethylsilyl cyanide under the action of a catalyst A to obtain a compound as shown in a formula (I), wherein the catalyst A is magnesium diiodide, magnesium dibromide and magnesium perchlorate, (b) carrying out catalytic hydrogenation reaction on the compound as shown in the formula (I) to obtain (S)-2-cyano piperidine as shown in a formula (II), and (c) hydrolyzing the compound as shown in the formula (II) to obtain (S)-2-piperidinecarboxylic acid as shown in a formula (III). The preparation method utilizes cheap and easily available organic raw materials, and has the advantages of simple operation, mild reaction conditions, good stereoselectivity, high yield and the like.
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 (2021/08/12)
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 0111-0120, (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.
