(2S,4R)-4-Methylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4R)-4-Methylpyrrolidine-2-carboxylic acid
• CAS No.: 23009-50-9
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.15704
• DSSTox Substance ID: DTXSID201314084
• Nikkaji Number: J826.447C
• Wikidata: Q27463414
• Mol file: 23009-50-9.mol

Synonyms:(2S,4R)-4-Methylpyrrolidine-2-carboxylic acid;(4R)-4-methyl-L-proline;23009-50-9;trans-4-methyl-L-proline;Rel-(2S,4R)-4-methylpyrrolidine-2-carboxylic acid;13532-73-5;trans-4-Methylprolin;SCHEMBL1355142;DTXSID201314084;AKOS006348102;CS-0184636;(2S, 4R)-4-methylpyrrolidine-2-carboxylic acid;EN300-6999687;Q27463414

Chemical Property of (2S,4R)-4-Methylpyrrolidine-2-carboxylic acid

Chemical Property:

• Melting Point: 230-238 °C
• Boiling Point: 250.2±33.0 °C(Predicted)
• PKA: 2.36±0.40(Predicted)
• PSA: 49.33000
• Density: 1.104±0.06 g/cm3(Predicted)
• LogP: 0.39780
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

Trans-4-Methyl-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(NC1)C(=O)O
• Isomeric SMILES: C[C@@H]1C[C@H](NC1)C(=O)O

Technology Process of (2S,4R)-4-Methylpyrrolidine-2-carboxylic acid

There total 33 articles about (2S,4R)-4-Methylpyrrolidine-2-carboxylic 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: 88.0%

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → trans-4-methyl-L-proline (23009-50-9)

Guidance literature:

With borane-ammonia complex; recombinant leucine hydroxylase; oxygen; iron(II); α-ketoglutaric acid disodium salt;

DOI:10.1021/acs.joc.8b00248

Reference yield: 87.0%

(2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester (119595-87-8) → trans-4-methyl-L-proline (23009-50-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 16h;

DOI:10.1021/jo00269a022

Reference yield:

C6H9NO2 → trans-4-methyl-L-proline (23009-50-9)

Guidance literature:

With borane-ammonia complex; In aq. phosphate buffer; at 20 ℃; for 4h; pH=7;

DOI:10.1016/j.tet.2018.09.046

upstream raw materials:

C₈H₁₆ClNO₂

(2S,4R)-4-methyl-N-(9-(9-phenylfluorenyl))proline tert-butyl ester

1-tert-butyl 2-methyl (2S,4R)-4-methylpyrrolidine-1,2-dicarboxylate

2-methylpropenal

Downstream raw materials:

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester

N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine benzyl ester

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid

Refernces

• 1、 Zwick, Christian R.,Renata, Hans. "A one-pot chemoenzymatic synthesis of (2S, 4R)-4-methylproline enables the first total synthesis of antiviral lipopeptide cavinafungin B". . p. 6469 - 6473. Retrieved 2018/10/05.
• 2、 Fukuhara, Kazuya,Takada, Kentaro,Okada, Shigeru,Matsunaga, Shigeki. "Nazumazoles A-C, cyclic pentapeptides dimerized through a disulfide bond from the marine sponge theonella swinhoei". . p. 2646 - 2648. Retrieved 2015/06/16.