(s)-3-Hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione

Base Information

• Chemical Name: (s)-3-Hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione
• CAS No.: 254730-06-8
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.24
• DSSTox Substance ID: DTXSID501174198
• Mol file: 254730-06-8.mol

Synonyms:(s)-3-hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione;254730-06-8;DTXSID501174198;(3S)-3-Hydroxy-1-[(4-methoxyphenyl)methyl]-2,5-pyrrolidinedione

Chemical Property of (s)-3-Hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 235.08445790
• Heavy Atom Count: 17
• Complexity: 310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CN2C(=O)CC(C2=O)O
• Isomeric SMILES: COC1=CC=C(C=C1)CN2C(=O)C[C@@H](C2=O)O

Technology Process of (s)-3-Hydroxy-1-(4-methoxybenzyl)pyrrolidine-2,5-dione

There total 3 articles about (s)-3-Hydroxy-1-(4-methoxybenzyl)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%

(S)-Malic acid (97-67-6,78644-42-5) + 4-methoxy-benzylamine (2393-23-9) → (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione (254730-06-8)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; for 8h; optical yield given as %ee; Reflux;

DOI:10.1016/j.tetasy.2011.01.012

Reference yield: 91.0%

acetic acid (3S)-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester (174874-82-9) → (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione (254730-06-8)

Guidance literature:

With ethanol; acetyl chloride; at 50 ℃; for 5h;

DOI:10.1016/S0957-4166(99)00395-X

Reference yield:

4-methoxy-benzylamine (2393-23-9) → (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione (254730-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Reflux

1.2: Reflux

1.3: Reflux

2.1: ethanol; acetyl chloride / 20 °C

With ethanol; acetyl chloride;

DOI:10.1016/j.tetasy.2011.01.012

upstream raw materials:

acetic acid (3S)-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester

(S)-Malic acid

4-methoxy-benzylamine

Downstream raw materials:

1-[(4-methoxyphenyl)methyl]-2,5-pyrrolidinedione

C₂₉H₃₃NO₈S₂

(S)-4-Benzyloxy-5-(3-benzyloxy-propyl)-5-hydroxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one

(+)-(4S,5R)-4-benzyloxy-5-(3'-benzyloxypropyl)-1-(4-methoxybenzyl)-2-pyrrolidinone