31551-66-3

Basic information

• Product Name: (4S)-4-methyl-2-Pyrrolidinone
• CAS NO: 31551-66-3
• Molecular Formula: C5H9NO
• Molecular Weight: 99.1326
• Mol File: 31551-66-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (4S)-4-methyl-2-Pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-methyl-2-Pyrrolidinone(31551-66-3)
• EPA Substance Registry System: (4S)-4-methyl-2-Pyrrolidinone(31551-66-3)

Safety Data

• Hazardous Substances Data: 31551-66-3(Hazardous Substances Data)

Usage

General Description

(4S)-4-methyl-2-Pyrrolidinone is a chemical compound with the molecular formula C5H9NO. It is a colorless liquid with a faint amine-like odor, and it is commonly used as a solvent in various industrial applications, such as in the production of pharmaceuticals, polymers, and agrochemicals. It is also used as a reaction medium in organic synthesis and as a solubilizer for drugs and polymers. Additionally, (4S)-4-methyl-2-Pyrrolidinone exhibits high chemical stability, low toxicity, and good solvating properties, making it a versatile and widely used solvent in the chemical and pharmaceutical industry. However, it is important to handle this compound with care, as it may cause skin and eye irritation upon contact.

Upstream product

• 492435-27-5 (2S,5S)-N-allyl-2-(tert-butyldimethylsilyl)oxy-2-bromomethyl-5-phenyl-1,3-oxazolidin-4-one 
• 492435-12-8 (2S,6R,7aS)-7a-(tert-butyldimethylsilyl)oxy-6-methyl-2-phenyltetrahydropyrrolo[2,1-b]oxazol-3-one 

Downstream Products

• 128112-22-1 (S)-3-methyl-4-aminobutyric acid 

Relevant articles and documents

Asymmetric synthesis of β-substituted γ-lactams employing the samp-/ramp-hydrazone methodology. Application to the synthesis of (R-(-)-baclofen

A short and efficient asymmetric synthesis of β-substituted γ-lactams is described. Key steps are the α-alkylation of aldehyde SAMP-hydrazones with alkyl bromoacetates, their MMPP mediated conversion to the corresponding nitriles and a reductive cyclization with Raney Ni or Ni boride to the title pyrrolidin-2-ones. The β-substituted γ-lactams are obtained in three steps, good overall yields (27-78%) and excellent enantiomeric excesses (ee=93-99%). The applicability of this procedure for the asymmetric synthesis of GABAs (γ-aminobutyric acids) is demonstrated for (R-(-)-baclofen hydrochloride, which is obtained in 4 steps 55% yield and 94% ee.

Stereoselective formation of optically active 2-oxy-1,3-oxazolidin-4-ones and an efficient synthesis of optically active secondary 2-pyrrolidones

Treatment of (-)-O-acyllactamides or mandelamides with TBSOTf in the presence of base gives optically active 2-oxy-1,3-oxazolidin-4-ones stereoselectively, which serve as useful precursors for the preparation of optically active secondary 2-pyrrolidones via radical cyclization and subsequent one-step removal of mandelic acid.

The Synthesis of Aracemic 4-Substituted Pyrrolidinones and 3-Substituted Pyrrolidines. An Asymmetric Synthesis of (-)-Rolipram

Conjugate additions of RCuCNLi to the chiral α,β-unsaturated lactam 4 gives almost exclusive exo addition - a reversal in stereochemistry when cuprates were added to chiral lactam 1.The lactams 5 were transformed into 4-substituted pyrrolidinones 8 via a three-step sequence which involved decarbalkoxylation, silane reduction and metal-ammonia benzylamine cleavage.The chemical yields as well as the enantiomeric purity were very high for this process.As an example of the usefulness of this scheme, the antidepressant (-)-Rolipram was prepared in good overall yield.Furthermore, the bicyclic lactams 6 were readily transformed, using alane as the reducing agent, to 3-substituted pyrrolidines 11.Absolute configurations of 8 and 11 were confirmed by comparison with literature assignments which also gave strong support to the facial addition of the cuprates to 4.