63328-12-1

Basic information

• Product Name: (5R)-5-1-Methylethyl-2-Pyrrolidinone
• Synonyms: (5R)-5-1-Methylethyl-2-Pyrrolidinone;(5R)-5-Isopropyl-2-pyrrolidinone;(5R)-5-Isopropyl-2-pyrrolidinone,99%e.e.;(R)-5-isopropylpyrrolidin-2-one;2-Pyrrolidinone, 5-(1-methylethyl)-, (5R)-
• CAS NO: 63328-12-1
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.18422
• Mol File: 63328-12-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5R)-5-1-Methylethyl-2-Pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-5-1-Methylethyl-2-Pyrrolidinone(63328-12-1)
• EPA Substance Registry System: (5R)-5-1-Methylethyl-2-Pyrrolidinone(63328-12-1)

Safety Data

• Hazardous Substances Data: 63328-12-1(Hazardous Substances Data)

Usage

Description

(5R)-5-1-Methylethyl-2-Pyrrolidinone, also known as 5-Methyl-2-pyrrolidinone, is a chemical compound belonging to the class of pyrrolidinones. It is a colorless liquid with a faint amine-like odor and is miscible with water. (5R)-5-1-Methylethyl-2-Pyrrolidinone is characterized by the presence of a chiral center, making it a potential chiral auxiliary in asymmetric synthesis. It is widely used in various industrial applications, including the production of pharmaceuticals, agrochemicals, and polymers.

Uses

Used in Pharmaceutical Industry:
(5R)-5-1-Methylethyl-2-Pyrrolidinone is used as a solvent and reactant in the synthesis of various pharmaceutical compounds. Its ability to dissolve a wide range of substances and participate in chemical reactions makes it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, (5R)-5-1-Methylethyl-2-Pyrrolidinone serves as a key component in the production of various agrochemicals. Its versatility as a solvent and reactant allows for the creation of effective and targeted agricultural products.
Used in Polymer Industry:
(5R)-5-1-Methylethyl-2-Pyrrolidinone is utilized in the synthesis of polymers, contributing to the development of new materials with specific properties. Its role in polymer production enhances the versatility and applicability of the resulting polymers in various industries.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
Due to its chiral center, (5R)-5-1-Methylethyl-2-Pyrrolidinone has the potential to act as a chiral auxiliary in asymmetric synthesis. This application is crucial in the production of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical processes.

Upstream product

• 41654-04-0 5-Methyl-4-oxohexanoic acid 
• 54857-48-6 ethyl 5-methyl-4-oxohexanoate 
• 147778-56-1 tert-butyl (R)-2-isopropyl-5-oxopyrrolidine-1-carboxylate 

Relevant articles and documents

Approaches to the total synthesis of chaetochalasin A

Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels-Alder reactions. Approaches to the total synthesis of chaetochalasin A using this approach have been studied. Methyl (6R,8S,2Z,4E,10E,12E,14E)-6,8,10,14-tetramethylhexadeca-2,4,10,12,14-pentaenoate was identified as a key intermediate and was synthesized from (E)-1-bromo-4-tert-butyldimethylsilyloxy-2-methylbut-2-ene using diastereoselective alkylations of derivatives of (+)-pseudoephedrine to introduce the stereogenic centres, a modified Julia reaction to prepare the conjugated triene and a phosphonate condensation to provide the (2Z)-alkene. However, during the synthesis, facile geometrical isomerisation of the (14E)-trisubstituted and (2Z)-double-bonds was observed and attempts to incorporate this pentaene into a synthesis of chaetochalasin A led to the formation of mixtures of products. The analogous ethyl 6,8,10,14-tetramethylhexadeca-4,10,12,14-tetraenoate [that lacks the (2Z)-double-bond] was incorporated into a Diels-Alder precursor by acylation of a valine-derived N-acylpyrrolidinone followed by oxidative elimination of the corresponding 3-(phenylselanyl)pyrrolidinone. However, preliminary studies of the macrocycle-forming Diels-Alder reaction for a synthesis of chaetochalasin A were complicated by (E,Z)-isomerisation of the (10E)-double-bond of the conjugated triene and three Diels-Alder adducts were isolated and characterised. Further studies of this approach to chaetochalasin A will require an alternative procedure for the generation of the acylpyrrolinone in the presence of the acid sensitive conjugated triene.

Synthesis of γ-, δ-, and ε-lactams by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters

Highly enantiomerically enriched γ- and δ-lactams have been prepared by a simple and very efficient procedure that involves the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters followed by desulfinylation of the nitrogen atom and spo