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

Base Information

• Chemical Name: (2S,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid
• CAS No.: 336818-78-1
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.347
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID90373174
• Wikidata: Q72450331
• Mol file: 336818-78-1.mol

Synonyms:336818-78-1;(2S,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid;(2S,4R)-Boc-4-phenyl-pyrrolidine-2-carboxylic acid;(2S,4R)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylpyrrolidine-2-carboxylic acid;cis-1-(tert-Butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid;(2S,4R)-Boc-4-phenyl-Pro-OH;MFCD06656435;(2S,4R)-Boc-4-phenylpyrrolidine-2-carboxylic acid;SCHEMBL1243964;DTXSID90373174;JDAQDIQHICLYKH-STQMWFEESA-N;(2S,4R)-1-(tert-Butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylicacid;AKOS015919063;AS-50494;A5987;CS-0054186;P10369;(4R)-1-(tert-Butoxycarbonyl)-4-phenyl-L-proline;cis-1-(Boc)-4-Phenylpyrrolidine-2-carboxylic acid;(2S,4R)-1-(BOC)-4-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID;(2S,4R)-1-[(tert-Butoxy)carbonyl]-4-phenylpyrrolidine-2-carboxylic acid;(2S,4R)-4-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

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

Chemical Property:

• Vapor Pressure: 1.43E-08mmHg at 25°C
• Refractive Index: 1.548
• Boiling Point: 441.5 °C at 760 mmHg
• PKA: 3.90±0.40(Predicted)
• Flash Point: 220.8 °C
• PSA: 66.84000
• Density: 1.196 g/cm³
• LogP: 2.80210
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 396

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-Boc-4-phenyl-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)C2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)C2=CC=CC=C2

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

There total 15 articles about (2S,4R)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-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: 78.0%

(S)-1-(tert-butoxycarbonyl)-4-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylic acid → (2S,4R)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid (336818-78-1,158567-91-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol;

DOI:10.1021/jm501145a

Reference yield: 78.0%

C12H13NO2*ClH → (2S,4R)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid (336818-78-1,158567-91-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol;

DOI:10.1021/jm501145a

Reference yield: 64.0%

(2S,4R)-4-hydroxy-4-phenylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester → (2S,4R)-1-(tert-butoxycarbonyl)-4-phenyl-2-pyrrolidinecarboxylic acid (336818-78-1,158567-91-0)

Guidance literature:

(2S,4R)-4-hydroxy-4-phenylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester; With trifluoroacetic acid; for 38h;

With di-tert-butyl dicarbonate; triethylamine; In water; at 20 ℃; for 4h;

With palladium 10% on activated carbon; hydrogen; In methanol; for 2h; under 760.051 Torr;

DOI:10.1021/acs.orglett.8b00364

upstream raw materials:

(2S,4R)-4-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

di-tert-butyl dicarbonate

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4R)-2-((S)-1-Methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

C₁₈H₂₁NO

(2S,4R)-4-Phenyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(2S,4R)-2-[4-(4-cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester