5336-34-5

Usage

Appearance

White solid

Molecular weight

205.25 g/mol

Melting point

108-111°C

Family

Pyrrolidin-2-one derivatives

Applications

Organic synthesis, pharmaceutical research

Usage

Building block in the synthesis of pharmaceuticals and fine chemicals

Biological activities

Antioxidant properties, enzyme activity modulation

Significance

Valuable intermediate in the production of pharmaceuticals and other bioactive compounds

Upstream product

• 58486-00-3 1-benzylpyrrolidine-2,3-dione 
• 5291-77-0 1-benzyl-2-pyrrolidone 
• 100-46-9 benzylamine 
• 29897-82-3 N-benzylpyrrolidine 
• 77868-77-0 N-benzyl-2,4-dibromobutyramide 
• 100372-86-9 3-acetoxy-1-benzyl-2-pyrrolidinone 

Downstream Products

• 100372-86-9 3-acetoxy-1-benzyl-2-pyrrolidinone 
• 101793-67-3 phenyl-carbamic acid-(1-benzyl-2-oxo-pyrrolidin-3-yl ester) 

Relevant academic research and scientific papers

Electrochemical deamination of alkoxyamine lactams

An anodic electrochemical deamination of 3-alkoxyamine lactams to 3-hydroxy lactams was developed. The electrochemical transformation was achieved by using reticulated vitreous carbon (RVC) and stainless-steel electrodes in aqueous ethanolic solution of NaOAc. This simple electrochemical procedure represents an ecofriendly alternative to the traditional chemical reductive deamination, which requires of a large excess of Zn (up to 40 equivalents) and acetic acid.

Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.

Transition Metal-Free Selective Double sp3 C-H Oxidation of Cyclic Amines to 3-Alkoxyamine Lactams

The first chemical method for selective dual sp3 C-H functionalization at the alpha-and beta positions of cyclic amines to their corresponding 3-alkoxyamine lactams is reported. Unlike traditional Cα-H oxidation of amines to amides mediated by transition metals, the present protocol, which involves the use of NaClO2/TEMPO/NaClO in either aqueous or organic solvent, not only allows the Cα-H oxidation but also the subsequent functionalization of the unreactive β-methylene group in an unprecedented tandem fashion and using environmentally friendly reactants.

Chemoenzymatic enantioselective synthesis of 3-hydroxy-2-pyrrolidinones and 3-hydroxy-2-piperidinones

The enantioselective synthesis of 3-hydroxypyrrolidin-2-ones and 3-hydroxy piperidin-2-ones has been carried out in high enantiomeric excess employing immobilized lipase from Pseudomonas cepacia.