2-Benzyl 1-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 2-Benzyl 1-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate
• CAS No.: 203645-44-7
• Molecular Formula: C24H27NO5
• Molecular Weight: 409.47
• DSSTox Substance ID: DTXSID60572273
• Wikidata: Q82460567
• Mol file: 203645-44-7.mol

Synonyms:203645-44-7;2-Benzyl 1-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate;2-O-benzyl 1-O-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(phenylmethyl)-, 1-(1,1-dimethylethyl) 2-(phenylmethyl) ester, (2S,4R)-;SCHEMBL12643706;DTXSID60572273;(4R)-BOC)-4-BENZYL-PYR-OBZL;J-013245;(4R)-Boc-4-benzyl-Pyr-OBzl, >=96.0% (HPLC);2-Benzyl 1-(tert-butyl) (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate

Chemical Property of 2-Benzyl 1-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 1.83E-12mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 557.5°C at 760 mmHg
• Flash Point: 290.9°C
• PSA: 72.91000
• Density: 1.204g/cm³
• LogP: 4.06260
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 409.18892296
• Heavy Atom Count: 30
• Complexity: 614

Purity/Quality:

98%,99%, ^*data from raw suppliers

(4R)-Boc-4-benzyl-Pyr-OBzl ≥96.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(CC(C1=O)CC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H](C[C@H](C1=O)CC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3

Technology Process of 2-Benzyl 1-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate

There total 5 articles about 2-Benzyl 1-tert-butyl (2S,4R)-4-benzyl-5-oxopyrrolidine-1,2-dicarboxylate 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:

benzyl bromide (100-39-0) + benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) → (2S,4R)-4-Benzyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (203645-44-7)

Guidance literature:

With lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 2 h;

DOI:10.1016/S0040-4020(97)10399-4

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,4R)-4-Benzyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (203645-44-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NEt₃ / CH₂Cl₂

2: 1.) LiHMDS / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 2 h

With triethylamine; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1016/S0040-4020(97)10399-4

Reference yield:

benzyl chloride (100-44-7) → (2S,4R)-4-Benzyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (203645-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / tetrahydrofuran / 120 h / Heating

2: NEt₃ / CH₂Cl₂

3: 1.) LiHMDS / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 2 h

With triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(97)10399-4

upstream raw materials:

benzyl bromide

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

di-tert-butyl dicarbonate

benzyl chloride

Downstream raw materials:

(2S,4R)-4-Benzyl-2-tert-butoxycarbonylamino-5-oxo-5-phenyl-pentanoic acid benzyl ester