(2S,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate
• CAS No.: 1499-56-5
• Molecular Formula: C6H11 N O3
• Molecular Weight: 145.158
• DSSTox Substance ID: DTXSID50426716
• Nikkaji Number: J705.326F
• Wikidata: Q82239544
• ChEMBL ID: CHEMBL1194431
• Mol file: 1499-56-5.mol

Synonyms:1499-56-5;(2S,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate;Methyl (2S,4R)-4-Hydroxypyrrolidine-2-Carboxylate;L-Proline, 4-hydroxy-, methyl ester, (4R)-;trans-4-hydroxy-L-proline methyl ester;methyl (4R)-4-hydroxy-L-prolinate;(2S,4R)-methyl4-hydroxypyrrolidine-2-carboxylate;SCHEMBL589711;4beta-Hydroxy-L-proline methyl;CHEMBL1194431;DTXSID50426716;4(R)-Hydroxyproline methyl ester;ZORHSASAYVIBLY-UHNVWZDZSA-N;MFCD00797543;AKOS000278432;BS-9865;EN300-145902;A854551;EN300-27730193;methyl (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylate;rac-methyl (2R,4S)-4-hydroxypyrrolidine-2-carboxylate;trans-4-Hydroxy-L-proline methyl ester (H-L-Hyp-OMe);4(R)-hydroxypyrrolidine-2(S)-carboxylic acid methyl ester;(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid methyl ester;(2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester;(2S,4R)-2-CARBOMETHOXY-4-HYDROXYPYRROLIDINE HYDROCHLORIDE

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

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Melting Point: 156-160 °C
• Refractive Index: 1.487
• Boiling Point: 247.177°C at 760 mmHg
• PKA: 14.44±0.40(Predicted)
• Flash Point: 103.289°C
• PSA: 58.56000
• Density: 1.216g/cm³
• LogP: -0.78900
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 145.07389321
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

98.5% ^*data from raw suppliers

(2S,4R)-Methyl4-Hydroxypyrrolidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1)O
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H](CN1)O
• Uses: (2S,4R)-Methyl 4-Hydroxypyrrolidine-2-carboxylate is used in preparation of Pyridazinamine derivatives as modulators of SMARCA2 and BRM target proteins.

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

There total 12 articles about (2S,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate 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: 100.0%

methanol (67-56-1) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → (R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2)

Guidance literature:

With thionyl chloride;

DOI:10.1021/jo00305a007

Reference yield: 100.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20 ℃; for 4h;

Reference yield: 100.0%

acetyl chloride (75-36-5) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → (R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2)

Guidance literature:

In methanol; for 16h; Reflux;

DOI:10.1002/ejoc.201201068

upstream raw materials:

diazomethane

4R-4-hydroxyproline

methanol

diethyl ether

Downstream raw materials:

(4R,5S,6S)-3-[(3S,5S)-5-[(2-Hydroxy-ethanesulfonylamino)-methyl]-1-(4-methoxy-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(4R,5S,6S)-3-[(3S,5S)-5-(Carbamoylmethanesulfonylamino-methyl)-1-(4-methoxy-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-1-(4-methoxy-benzyloxycarbonyl)-5-[(morpholine-4-sulfonylamino)-methyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

5-[(2S,4S)-1-(4-Methoxy-benzyloxycarbonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1,1-dioxo-1λ⁶-[1,2,5]thiadiazolidine-2-carboxylic acid 4-methoxy-benzyl ester

Refernces

• 1、 -. "As Aurora kinase inhibitor derivatives". Paragraph 0612; 0615; 0616. . Retrieved 2019/06/27.
• 2、 -. "CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE". Paragraph 00576-00578. . Retrieved 2019/06/11.