874130-13-9

Basic information

• Product Name: Methyl 1-Benzyl-5-thioxopyrrolidine-3-carboxylate
• Synonyms: Methyl 1-Benzyl-5-thioxopyrrolidine-3-carboxylate
• CAS NO: 874130-13-9
• Molecular Formula: C₁₃H₁₅NO₂S
• Molecular Weight: 249.3287
• Product Categories: Esters;Pyrrolidines
• Mol File: 874130-13-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 1-Benzyl-5-thioxopyrrolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1-Benzyl-5-thioxopyrrolidine-3-carboxylate(874130-13-9)
• EPA Substance Registry System: Methyl 1-Benzyl-5-thioxopyrrolidine-3-carboxylate(874130-13-9)

Safety Data

• Hazardous Substances Data: 874130-13-9(Hazardous Substances Data)

Upstream product

• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 97-65-4 2-methylenesuccinic acid 
• 5733-86-8 1-benzyl-5-oxopyrrolidine-3-carboxylic acid 
• 100-46-9 benzylamine 

Downstream Products

• 500136-11-8 1-benzyl-5-(2-ethoxycarbonyl-2-hydrazinyl-1-yliden)-pyrrolidine-3-carboxylic acid methyl ester 

Relevant articles and documents

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.