(2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid
• CAS No.: 132622-85-6
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 240.259
• DSSTox Substance ID: DTXSID80564615
• Wikidata: Q72459185
• Mol file: 132622-85-6.mol

Synonyms:132622-85-6;(2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;(2R,4R)-4-cyano-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(4R)-1-(tert-Butoxycarbonyl)-4-cyano-D-proline;(4R)-1-Boc-4-cyano-D-proline;SCHEMBL2707931;DTXSID80564615;MIVXQYMYEMUMKK-JGVFFNPUSA-N;MFCD14582688;A26550;(2R,4R)-1-(t-Butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;(2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylicacid

Chemical Property of (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid

Chemical Property:

• Melting Point: 134-135℃
• Boiling Point: 423.5±45.0 °C(Predicted)
• PKA: 3.51±0.40(Predicted)
• PSA: 90.63000
• Density: 1.25
• LogP: 1.15808
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 240.11100700
• Heavy Atom Count: 17
• Complexity: 377

Purity/Quality:

97% ^*data from raw suppliers

(4R)-1-Boc-4-cyano-D-proline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)C#N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@@H]1C(=O)O)C#N

Technology Process of (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid

There total 4 articles about (2R,4R)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-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: 90.0%

(4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester (132622-83-4) → (2R,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-85-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 22 ℃;

DOI:10.1021/jo00009a016

Reference yield:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) → (2R,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / CBr₄, P(Ph₃) / CH₂Cl₂ / 16 h / 22 °C

2: 22 percent / n-Bu₄NCN / dimethylformamide / 20 h / 55 °C

3: 90 percent / 1M NaOH / methanol; H₂O / 22 °C

With sodium hydroxide; carbon tetrabromide; tetra-n-butylammonium cyanide; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

Reference yield:

(4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester (132622-76-5) → (2R,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 22 percent / n-Bu₄NCN / dimethylformamide / 20 h / 55 °C

2: 90 percent / 1M NaOH / methanol; H₂O / 22 °C

With sodium hydroxide; tetra-n-butylammonium cyanide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

upstream raw materials:

(4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester

(4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester

Downstream raw materials:

(4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline

(2R,4S)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(4R)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-D-proline