(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

Base Information

• Chemical Name: (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride
• CAS No.: 144527-44-6
• Molecular Formula: C11H19NO5^.HCl
• Molecular Weight: 281.736
• European Community (EC) Number: 609-795-4
• ChEMBL ID: CHEMBL552640
• DSSTox Substance ID: DTXSID50932327
• Mol file: 144527-44-6.mol

Synonyms:40216-83-9;(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride;H-Hyp-OMe.HCl;trans-4-Hydroxy-L-proline methyl ester hydrochloride;Methyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate Hydrochloride;L-4-Hydroxyproline methyl ester hydrochloride;H-HYP-OME HCL;MFCD00080855;H-Hyp-OMe (hydrochloride);hydroxyproline methyl ester hydrochloride;methyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate;hydrochloride;(2S,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate HCl;1001333-91-0;L-4-trans-Hydroxyproline methyl ester hydrochloride salt;KLGSHNXEUZOKHH-JBUOLDKXSA-N;Methyl trans-4-Hydroxypyrrolidine-2-carboxylate Hydrochloride;H-Hyp-OMe-HCl;Hyp-OMe. HCl;L-Proline, 4-hydroxy-, methyl ester, hydrochloride, (4R)-;H-Hyp-OMe hydrochloride;SCHEMBL133898;CHEMBL552640;DTXSID50932327;(2S,4R)-methyl4-hydroxypyrrolidine-2-carboxylatehydrochloride;CS-M0623;AKOS000278437;AKOS015924093;AC-4514;PS-8529;HY-76043;L-hydroxyproline methylester hydrochloride;L-hydroxyproline methylester-hydrochloride;L-hydroxyproline methylester.hydrochloride;L-hydroxyproline rnethylester hydrochloride;(4R)-4-Hydroxy-L-proline methyl ester HCl;A7333;AM20100071;EN300-72831;methyl (4R)-4-hydroxy-L-prolinate hydrochloride;trans-4-hydroxyproline methyl ester hydrochloride;trans-L-Hydroxyproline methyl ester hydrochloride;L-HYDROXYPROLINE METHYL ESTER HYDROCHLORIDE;(2S,4R)-4-hydroxyproline methyl ester hydrochloride;J-300156;Q-101694;Methyl 4-hydroxyprolinatato--hydrogen chlorido (1/1);trans-4-hydroxy-l-proline methylester hydrochloride salt;trans-4-Hydroxy-L-proline, methyl ester, hydrochloride;(2S,4R)-2-methoxycarbonyl-4-hydroxypyrrolidine hydrochloride;(2S,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride;(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate HCl salt;(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate-HCl salt;L-4-Hydroxyproline methyl ester hydrochloride, >=98.0% (TLC);(2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester HCl;(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate, hydrochloride;Methyl (2S,4R)-4-hydroxy-2-pyrrolidinecarboxylate Hydrochloride;methyl (2s,4r)-4-hydroxypyrrolidine-2-carboxylate hydrochloride salt;(2S,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride;4(R)-hydroxypyrrolidine-2(S)-carboxylic acid methyl ester hydrochloride;(2S, 4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride;336192-08-6

Chemical Property of (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

Chemical Property:

• PSA: 76.07000
• LogP: 1.26960
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 181.0505709
• Heavy Atom Count: 11
• Complexity: 137

Purity/Quality:

99.3% ^*data from raw suppliers

(2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER HCL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1)O.Cl
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H](CN1)O.Cl

Technology Process of (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

There total 2 articles about (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride 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:

di-tert-butyl dicarbonate (24424-99-5) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 20 ℃;

DOI:10.1002/anie.201302014

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / methanol / 15 h / 0 - 20 °C

2: triethylamine / acetonitrile / 0 - 20 °C

With thionyl chloride; triethylamine; In methanol; acetonitrile;

DOI:10.1002/anie.201302014

Reference yield: 88.0%

(2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6) + p-toluenesulfonyl chloride (98-59-9) → (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88043-21-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1002/anie.201302014

upstream raw materials:

4R-4-hydroxyproline

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S,4R)-1-benzyl-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid methyl ester

(2S,4R)-1-benzyl-4-hydroxyproline methyl ester

(2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Refernces