(2S)-3-Pyrroline-1,2alpha-dicarboxylic acid 1-benzyl 2-methyl ester

Base Information

• Chemical Name: (2S)-3-Pyrroline-1,2alpha-dicarboxylic acid 1-benzyl 2-methyl ester
• CAS No.: 5211-24-5
• Molecular Formula: C14H15NO4
• Molecular Weight: 261.277
• DSSTox Substance ID: DTXSID201150983
• Nikkaji Number: J2.413.568C
• Mol file: 5211-24-5.mol

Synonyms:SCHEMBL4039820;OHNVVZQWOFYUEJ-LBPRGKRZSA-N;DTXSID201150983;(2S)-3-Pyrroline-1,2alpha-dicarboxylic acid 1-benzyl 2-methyl ester;(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester;2-Methyl 1-(phenylmethyl) (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate;5211-24-5

Chemical Property of (2S)-3-Pyrroline-1,2alpha-dicarboxylic acid 1-benzyl 2-methyl ester

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 261.10010796
• Heavy Atom Count: 19
• Complexity: 361

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C=CCN1C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: COC(=O)[C@@H]1C=CCN1C(=O)OCC2=CC=CC=C2

Technology Process of (2S)-3-Pyrroline-1,2alpha-dicarboxylic acid 1-benzyl 2-methyl ester

There total 10 articles about (2S)-3-Pyrroline-1,2alpha-dicarboxylic acid 1-benzyl 2-methyl ester 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: 99.0%

(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester hydrochloride → (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5)

Guidance literature:

With N-(Benzyloxycarbonyloxy)succinimide; triethylamine; In tetrahydrofuran; water; at 20 ℃; for 12.5h;

Reference yield: 88.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (2S)-2,5-dihydro-1H-pyrrole-2-carboxylate hydrochloride (186145-08-4) → (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)84059-8

Reference yield: 87.0%

methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate (84062-30-6) → (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; at 25 ℃; for 1.5h;

DOI:10.1139/v82-419

upstream raw materials:

(R)-4-hydroxy-L-proline ethyl ester

methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate

N-(Benzyloxycarbonyloxy)succinimide

(2S)-2,5-dihydro-1H-pyrrole-2-carboxylate hydrochloride

Downstream raw materials:

(S)-3,4-Dihydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

3,4-dehydro-L-proline

(2S,3R,4S)-N-benzyloxycarbonyl-3,4-dihydroxyproline methyl ester

(2S,3R,4S)-(N-Benzyloxycarbonyl)-6,6-dicarboxy-3,4-methano-L-proline trimethyl ester

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