trans-1-Benzylpyrrolidine-2,5-dicarboxylic acid

Base Information

• Chemical Name: trans-1-Benzylpyrrolidine-2,5-dicarboxylic acid
• CAS No.: 93713-33-8
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.266
• DSSTox Substance ID: DTXSID901182002
• Mol file: 93713-33-8.mol

Synonyms:trans-1-Benzylpyrrolidine-2,5-dicarboxylic acid;93713-33-8;(2S,5S)-1-Benzylpyrrolidine-2,5-dicarboxylic acid;111139-11-8;DTXSID901182002;rel-(2R,5R)-1-(Phenylmethyl)-2,5-pyrrolidinedicarboxylic acid

Chemical Property of trans-1-Benzylpyrrolidine-2,5-dicarboxylic acid

Chemical Property:

• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(N(C1C(=O)O)CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1C[C@H](N([C@@H]1C(=O)O)CC2=CC=CC=C2)C(=O)O

Technology Process of trans-1-Benzylpyrrolidine-2,5-dicarboxylic acid

There total 5 articles about trans-1-Benzylpyrrolidine-2,5-dicarboxylic 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: 47.0%

trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine (90290-04-3,50990-24-4,17740-40-8,52321-06-9,90365-12-1) → rac-trans-1-Benzyl-2,5-dicarboxypyrrolidine (93713-33-8)

Guidance literature:

With sodium hydroxide; In water; at 23 ℃; for 8h;

DOI:10.1021/jo00023a037

Reference yield:

trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine (90290-04-3,50990-24-4,17740-40-8,52321-06-9,90365-12-1) → (2S,5S)-1-Benzylpyrrolidine-2,5-dicarboxylic acid (52321-07-0,90365-14-3,93713-33-8,111139-11-8)

Guidance literature:

With sodium hydroxide; In water; at 23 ℃; for 8h;

DOI:10.1021/jo00023a037

Reference yield:

(+/-)-trans-1-benzylpyrrolidine-2,5-dicarboxamide → (2S,5S)-1-benzylpyrrolidine-2,5-dicarboxamide + C13H16N2O3 + (2R,5R)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid (52321-07-0,93713-33-8,111139-11-8,90365-14-3)

Guidance literature:

With Rhodococcus erythropolis AJ₂₇₀ cells; In dimethyl sulfoxide; at 30 ℃; for 15h; pH=7; enantioselective reaction; aq. phosphate buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/jo300412j

upstream raw materials:

trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine

(2R,5R)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid; compound with 2-amino-1-(4-nitro-phenyl)-propane-1,3-diol

trans-N-benzylpyrrolidine-2,5-dicarbonitrile

Downstream raw materials:

(2R,5R)-1-Benzyl-pyrrolidine-2,5-dicarboxylic acid; compound with 2-amino-1-(4-nitro-phenyl)-propane-1,3-diol

1-Benzyl-[(2R,5R)-2,5-bis(hydroxymethyl)]pyrrolidine

(2R,5R)-2,5-Pyrrolidinedicarboxylic acid

(-)-(2S,5S)-N-benzyl-trans-2,5-bis(methoxycarbonyl)pyrrolidine