138078-58-7

Basic information

• Product Name: 5-HYDROXYMETHYL-3-METHYLPYRROLIDIN-2-ONE
• Synonyms: 2-Pyrrolidinone, 5-(hydroxymethyl)-3-methyl-, (3S-cis)- (9CI)
• CAS NO: 138078-58-7
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Mol File: 138078-58-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-HYDROXYMETHYL-3-METHYLPYRROLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXYMETHYL-3-METHYLPYRROLIDIN-2-ONE(138078-58-7)
• EPA Substance Registry System: 5-HYDROXYMETHYL-3-METHYLPYRROLIDIN-2-ONE(138078-58-7)

Safety Data

• Hazardous Substances Data: 138078-58-7(Hazardous Substances Data)

Usage

Chemical compound

5-HYDROXYMETHYL-3-METHYLPYRROLIDIN-2-ONE

Usage

reagent in organic synthesis and pharmaceutical research

Derivative of

pyrrolidinone

Functional groups

hydroxymethyl group, methyl group

Potential applications

building block for pharmaceutical synthesis, solvent in chemical reactions, reagent in material synthesis

Upstream product

• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 
• 170885-06-0 (2R,5S,7R)-2-(p-methoxyphenyl)-7-(phenylthio)-3-oxa-1-azabicyclo<3.3.0>octan-2-one 
• 170885-05-9 (2R,5S)-2-(p-methoxyphenyl)-3-oxa-1-azabicyclo<3.3.0>octan-8-one 
• 170885-07-1 (2R,5S)-2-(p-methoxyphenyl)-3-oxa-1-azabicyclo<3.3.0>oct-6-en-8-one 
• 171595-94-1 (2R,5S,7S)-2-(p-methoxyphenyl)-7-methyl-3-oxa-1-azabicyclo<3.3.0>octan-2-one 
• 138231-07-9 <3R-(3α,6β,7aα)>-6-methyl-3-phenyl-3H,5H-tetrahydropyrrolo<1,2-c>oxazol-5-one 

Downstream Products

• 189618-78-8 N-methyl-3,5-dimethylpyrrolidin-2-one 

Relevant articles and documents

Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu 3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals

2-Substituted amidyl radicals derived from 8a-d and 9a-d undergo acyl mode 5-exo-trig cyclisation to give 3,5-trans pyrrolidinones 11a-d and 14a-d as the major products in low diastereoselectivity (de = 9-36%). The steric nature of the nitrogen substituent attached to the amidyl radical does not have a significant effect on selectivity. The stereochemical outcome is opposite to that expected based upon applying the Beckwith rule.

Stereoselective methylations of bicyclic lactams derived from pyroglutamic acid

Reaction of the lithium enolate of (-)7 with iodomethane provides a stereoselective synthesis of (2R,4S)-4-amino-2-methylpentanamide derivatives.