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

Base Information

• Chemical Name: (3S)-1-Benzyl-3-(benzyloxy)pyrrolidine-2,5-dione
• CAS No.: 170711-05-4
• Molecular Formula: C18H17NO3
• Molecular Weight: 295.33200
• DSSTox Substance ID: DTXSID50452757
• Nikkaji Number: J808.486F
• Wikidata: Q82273574
• Mol file: 170711-05-4.mol

Synonyms:170711-05-4;(3S)-1-Benzyl-3-(benzyloxy)pyrrolidine-2,5-dione;DTXSID50452757;(3S)-N-Benzyl-3-(benzyloxy)succinimide

Chemical Property of (3S)-1-Benzyl-3-(benzyloxy)pyrrolidine-2,5-dione

Chemical Property:

• PSA: 46.61000
• LogP: 2.46880
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 295.12084340
• Heavy Atom Count: 22
• Complexity: 397

Purity/Quality:

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)OCC3=CC=CC=C3
• Isomeric SMILES: C1[C@@H](C(=O)N(C1=O)CC2=CC=CC=C2)OCC3=CC=CC=C3

Technology Process of (3S)-1-Benzyl-3-(benzyloxy)pyrrolidine-2,5-dione

There total 2 articles about (3S)-1-Benzyl-3-(benzyloxy)pyrrolidine-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: 92.0%

benzyl bromide (100-39-0) + (3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione (101469-91-4) → (S)-1-benzyl-3-(benzyloxy)pyrrolidine-2,5-dione (170711-05-4)

Guidance literature:

With silver(l) oxide; In diethyl ether; Ambient temperature;

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

Reference yield:

(S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione (129823-21-8,173353-34-9) → (S)-1-benzyl-3-(benzyloxy)pyrrolidine-2,5-dione (170711-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / AcCl / ethanol / 5 h / 50 °C

2: 92 percent / Ag₂O / diethyl ether / 48 h / Ambient temperature

With acetyl chloride; silver(l) oxide; In diethyl ether; ethanol;

DOI:10.1016/S0040-4020(98)00734-0

Reference yield: 99.0%

n-propylmagnesium bromide (927-77-5) + (S)-1-benzyl-3-(benzyloxy)pyrrolidine-2,5-dione (170711-05-4) → 1-benzyl-4-benzyloxy-5-hydroxy-5-propyl-pyrrolidin-2-one

Guidance literature:

In dichloromethane; at -15 ℃;

DOI:10.1055/s-2006-939695

upstream raw materials:

benzyl bromide

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

(S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione

Downstream raw materials:

(S)-1-Benzyl-4-benzyloxy-5-hydroxy-5-methyl-pyrrolidin-2-one

(S)-1-Benzyl-4-benzyloxy-5-butyl-5-hydroxy-pyrrolidin-2-one

(S)-1-Benzyl-4-benzyloxy-5-hydroxy-5-isobutyl-pyrrolidin-2-one

(S)-1,5-Dibenzyl-4-benzyloxy-5-hydroxy-pyrrolidin-2-one