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

Base Information

• Chemical Name: (2R,4S)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid
• CAS No.: 132622-80-1
• Molecular Formula: C₁₁H₁₆N₂O₄
• Molecular Weight: 240.259
• DSSTox Substance ID: DTXSID20564614
• Wikidata: Q72459183
• Mol file: 132622-80-1.mol

Synonyms:132622-80-1;(2R,4S)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;(2R,4S)-4-cyano-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(4S)-1-Boc-4-cyano-D-proline;SCHEMBL9637135;DTXSID20564614;MFCD14582689;CS-0433609;A26552;(4S)-1-(tert-Butoxycarbonyl)-4-cyano-D-proline;(2R,4S)-1-(t-Butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid;(2R,4S)-1-(tert-butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylicacid;(2R-trans)-1-(tert-Butoxycarbonyl)-4-cyanopyrrolidine-2-carboxylic acid

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

Chemical Property:

• 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

(2R,4S)-1-(TERT-BUTOXYCARBONYL)-4-CYANOPYRROLIDINE-2-CARBOXYLICACID ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 6 articles about (2R,4S)-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: 100.0%

trans-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester (132623-07-5) → (4S)-1-(tert-butoxycarbonyl)-4-cyano-D-proline (132622-80-1)

Guidance literature:

With sodium hydroxide; In methanol; water;

DOI:10.1021/jo00009a016

Reference yield:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) → (4S)-1-(tert-butoxycarbonyl)-4-cyano-D-proline (132622-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / pyridine / 22 °C

2: 72 percent / dimethylformamide / 20 h / 55 °C

3: 100 percent / NaOH / H₂O; methanol

With pyridine; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

Reference yield:

(4R)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>-D-proline ethyl ester (132622-75-4) → (4S)-1-(tert-butoxycarbonyl)-4-cyano-D-proline (132622-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / dimethylformamide / 20 h / 55 °C

2: 100 percent / NaOH / H₂O; methanol

With sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

upstream raw materials:

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

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

(4R)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>-D-proline ethyl ester

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride

Downstream raw materials:

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

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

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