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

Base Information

• Chemical Name: (2S,4R)-4-(aminomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS No.: 132622-72-1
• Molecular Formula: C11H20 N2 O4
• Molecular Weight: 244.29
• DSSTox Substance ID: DTXSID401145576
• Mol file: 132622-72-1.mol

Synonyms:132622-72-1;(2S,4R)-4-(aminomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2S,4R)-4-(aminomethyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2S,4R)-4-(Aminomethyl)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid;SCHEMBL9636995;VWFCKAANOBELKO-SFYZADRCSA-N;DTXSID401145576;(2S,4R)-4-(aminomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid;AKOS015919002;AS-80224;A2801;CS-0053420;P18747;(4R)-1-(tert-Butoxycarbonyl)-4-(aminomethyl)-L-proline;(2S,4R)-1-Boc-4-(Aminomethyl)-pyrrolidine-2-carboxylic acid;1-(1,1-Dimethylethyl) (2S,4R)-4-(aminomethyl)-1,2-pyrrolidinedicarboxylate

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

Chemical Property:

• Vapor Pressure: 3.91E-07mmHg at 25°C
• Refractive Index: 1.511
• Boiling Point: 389°C at 760 mmHg
• PKA: 3.72±0.40(Predicted)
• Flash Point: 189.1°C
• PSA: 92.86000
• Density: 1.197g/cm³
• LogP: 1.29350
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 244.14230712
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-4-(Aminomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid ^*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)CN
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)CN

Technology Process of (2S,4R)-4-(aminomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

There total 3 articles about (2S,4R)-4-(aminomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-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: 98.0%

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-71-0) → (4S)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-L-proline (132622-72-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; at 22 ℃; for 16h; under 23271.7 Torr;

DOI:10.1021/jo00009a016

Reference yield:

(4S)-1-(tert-butoxycarbonyl)-4-cyano-L-proline ethyl ester (132623-05-3) → (4S)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-L-proline (132622-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / 1M NaOH / methanol / 16 h / 22 °C

2: 98 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 16 h / 22 °C / 23271.7 Torr

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; ethanol; water;

DOI:10.1021/jo00009a016

Reference yield:

(2S,4R)-4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (132622-63-0) → (4S)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-L-proline (132622-72-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.0 g / dimethylsulfoxide / 55 h / 55 °C

2: 76 percent / 1M NaOH / methanol / 16 h / 22 °C

3: 98 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 16 h / 22 °C / 23271.7 Torr

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; ethanol; water; dimethyl sulfoxide;

DOI:10.1021/jo00009a016

upstream raw materials:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(4S)-1-(tert-butoxycarbonyl)-4-cyano-L-proline ethyl ester

(2S,4R)-4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Downstream raw materials:

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