(2S,3S)-3-Hydroxypipecolic Acid

Base Information

• Chemical Name: (2S,3S)-3-Hydroxypipecolic Acid
• CAS No.: 176019-05-9
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.158
• DSSTox Substance ID: DTXSID90449969
• Nikkaji Number: J714.313C
• Wikidata: Q82269520
• ChEMBL ID: CHEMBL403757
• Mol file: 176019-05-9.mol

Synonyms:176019-05-9;(2S,3S)-3-hydroxypiperidine-2-carboxylic acid;(2S,3S)-3-Hydroxypipecolic Acid;2-Piperidinecarboxylicacid,3-hydroxy-,(2S,3S)-(9CI);Rel-(2S,3S)-3-hydroxypiperidine-2-carboxylic acid;208649-02-9;CHEMBL403757;SCHEMBL12909421;DTXSID90449969;FDMYUQHVJYNDLI-WHFBIAKZSA-N;(2S,3S)-3?Hydroxypipecolic acid;CS-0449804;(2S,3S)-3-Hydroxypiperidine-2-carboxylicacid;2-Piperidinecarboxylic acid,3-hydroxy-,(2S,3S)-

Chemical Property of (2S,3S)-3-Hydroxypipecolic Acid

Chemical Property:

• PSA: 69.56000
• LogP: -0.48730
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 145.07389321
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(NC1)C(=O)O)O
• Isomeric SMILES: C1C[C@@H]([C@H](NC1)C(=O)O)O

Technology Process of (2S,3S)-3-Hydroxypipecolic Acid

There total 155 articles about (2S,3S)-3-Hydroxypipecolic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(2S,3R)-N-benzyloxycarbonyl-3-hydroxypiperidine-2-carboxylic acid (1021428-00-1) → (2R,3R)-3-hydroxypiperidine-1-carboxylic acis (56879-47-1,112241-70-0,119593-44-1,122088-79-3,208649-02-9,176019-04-8,176019-05-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 25 ℃; for 12h; under 4137.29 Torr;

DOI:10.1021/jo702749r

Reference yield: 94.0%

(2S,3R)-3-Hydroxy-piperidine-2-carboxylic acid tert-butyl ester → (2R,3R)-3-hydroxypiperidine-1-carboxylic acis (56879-47-1,112241-70-0,119593-44-1,122088-79-3,208649-02-9,176019-04-8,176019-05-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(99)00636-X

Reference yield: 93.0%

(+)-(2S,3R)-3-hydroxypiperidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester (317384-38-6) → (2R,3R)-3-hydroxypiperidine-1-carboxylic acis (56879-47-1,112241-70-0,119593-44-1,122088-79-3,208649-02-9,176019-04-8,176019-05-9)

Guidance literature:

With lithium hydroxide; In ethanol;

DOI:10.1016/S0040-4039(00)01527-6

upstream raw materials:

3-hydroxypyridine-2-carboxylic acid

3-acetoxy-1-acetyl-piperidine-2-carboxylic acid ethyl ester

N-acetyl-N-(3t-ethoxycarbonyl-allyl)-glycine ethyl ester

1-acetyl-3-oxo-piperidine-2-carboxylic acid ethyl ester

Refernces

• 1、 Smart, Tristan J.,Hamed, Refaat B.,Claridge, Timothy D.W.,Schofield, Christopher J.. "Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles". supporting information. . Retrieved 2019/11/26.
• 2、 Chavan, Subhash P.,Khairnar, Lalit B.,Pawar, Kailash P.,Chavan, Prakash N.,Kawale, Sanket A.. "Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, β-(+)-conhydrine and (-)-swainsonine using an aziridine derived common chiral synthon". . p. 50580 - 50590. Retrieved 2015/06/25.