(S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione

Base Information

• Chemical Name: (S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione
• CAS No.: 101469-91-4
• Molecular Formula: C11H11 N O3
• Molecular Weight: 205.213
• DSSTox Substance ID: DTXSID00449652
• Nikkaji Number: J2.321.328A
• Wikidata: Q72441353
• Mol file: 101469-91-4.mol

Synonyms:(S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione;101469-91-4;(3S)-1-BENZYL-3-HYDROXYPYRROLIDINE-2,5-DIONE;N-Benzyl-(3S)-hydroxysuccinimide;SCHEMBL2276626;DTXSID00449652;VCPKAWKGCQTPCR-VIFPVBQESA-N;(3S)-N-Benzyl-3-hydroxysuccinimide;AKOS015999523;CS-0363173;(S)-1-benzyl-3-hydroxy-2,5-pyrrolidine dione;(S)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione

Chemical Property of (S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione

Chemical Property:

• Melting Point: 110-111℃
• PSA: 57.61000
• Density: 1.385
• LogP: 0.24430
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 271

Purity/Quality:

99%, ^*data from raw suppliers

(S)-1-Benzyl-3-hydroxypyrrolidine-2,5-dione 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)N(C1=O)CC2=CC=CC=C2)O
• Isomeric SMILES: C1[C@@H](C(=O)N(C1=O)CC2=CC=CC=C2)O

Technology Process of (S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione

There total 7 articles about (S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione 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: 96.0%

(S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione (129823-21-8,173353-34-9) → (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione (101469-91-4)

Guidance literature:

With acetyl chloride; In ethanol; at 50 ℃;

DOI:10.1016/S0040-4039(96)02301-5

Reference yield: 85.0%

(S)-Malic acid (97-67-6,78644-42-5) + benzylamine (100-46-9) → (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione (101469-91-4)

Guidance literature:

In ethanol; Heating;

DOI:10.1021/jm00162a013

Reference yield:

3-benzoyloxy-1-benzyl-2,5-pyrrolidinedione (173353-28-1) → (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione (101469-91-4) + (3R)-1-benzyl-3-hydroxypyrrolidine-2,5-dione (165657-63-6)

Guidance literature:

With phosphate buffer; In 1,4-dioxane; at 25 ℃; for 2.5h; Yield given. Yields of byproduct given; lipase PS;

DOI:10.1246/bcsj.69.207

upstream raw materials:

(S)-Malic acid

benzylamine

(RS)-N-benzyl-3-hydroxypyrrolidine-2,5-dione

3-benzoyloxy-1-benzyl-2,5-pyrrolidinedione

Downstream raw materials:

3R-acetoxypyrrolidine-1-carboxylic acid tert-butyl ester

(S)-tert-butyl 3-acetoxypyrrolidine-1-carboxylate

(S)-1-benzyl-3-(benzyloxy)pyrrolidine-2,5-dione

(S)-1-benzyl-3-(tert-butyldimethylsilyloxy)pyrrolidine-2,5-dione

Refernces

• 1、 -. "Substituted pyrazolo[1,5-a]pyrimidine compound and pharmaceutical composition and application thereof". Paragraph 0137; 0139; 0140; 0151; 0152. . Retrieved 2019/03/28.
• 2、 -. "COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY". Page/Page column 101. . Retrieved 2014/09/29.