57740-61-1

Upstream product

• 73208-42-1 (R)-(-)-methyl 7-(5-hydroxymethyl-2-oxo-1-pyrrolidine)heptanoate 
• 64840-00-2 (R)-(-)-methyl 7-(5-formyl-2-oxo-1-pyrrolidine)heptanoate 
• 67040-46-4 (5R)-5-((tert-ethoxyethoxy)methyl)pyrrolidin-2-one 
• 4042-36-8 D-pyrrolidone-5-carboxylic acid 
• 64839-99-2 7-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-heptanoic acid methyl ester 
• 67087-17-6 methyl 7-((2R)-2-((1-ethoxyethoxy)methyl)-5-oxopyrrolidin-1-yl)heptanoate 
• 75584-24-6 7-[(R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-heptanoic acid methyl ester 
• 64700-65-8 methyl (2R)-pyroglutamate 
• 66673-40-3 (R)-5-hydroxymethylpyrrolidin-2-one 
• 695231-50-6 7-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-heptanoic acid ethyl ester 
• 346672-97-7 ethyl 7-[(2R)-2-(hydroxymethyl)-5-oxo-1-pyrrolidinyl]heptanoate 
• 346672-53-5 ethyl (R)-7-(2-formyl-5-oxopyrrolidin-1-yl)heptanoate 
• 36969-89-8 dimethyl 2-oxoheptylphosphonate 
• 64839-98-1 7-[(R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-heptanoic acid methyl ester 

Relevant academic research and scientific papers

Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-Pyrrolidinones-stereochemical and lower side-chain optimization.

A series of 7-[(5R)-substituted 2-oxo-1-pyrrolidinyl]-heptanoic acids were prepared, their isomeric purity determined, and pharmacologically evaluated. Lactams with affinity for the EP(4) receptor displayed agonist behavior. The lower side-chain of the la

Heterocyclic Prostaglandins. V. Synthesis of (12R,15S)-(-)-11-Deoxy-8-azaprostaglandin E1 and Related Compounds

The synthesis of (12R,15S)-(-)-11-deoxy-8-azaprostaglandin E1 ((R)-1a) and three diastereomers ((R)-2a, (S)-1a, and (S)-2a) starting from optically active pyroglutamic acid ((R)-3 and (S)-3) is reported.Esterification of (R)-3 and NaBH4 reduction gave (R)-(-)-5-hydroxymethyl-2-pyrrolidinone ((R)-5).Ethoxyethylation of (R)-5 and N-alkylation with methyl 7-bromoheptanoate, followed by acid treatment, provided (R)-hydroxymethyl pyrrolidinone ((R)-8).The Collins oxidation of (R)-8 gave (R)-(-)-methyl 7-(5-formyl-2-oxo-1-pyrrolidine)heptanoate ((R)-9), which served as a key intermediate.The Wittig reaction of (R)-9 and dimethyl 2-oxoheptylphosphonate gave the (R)-enone ((R)-10a) which was converted to the (12R,15S)-enol ((R)-11a) and (12R,15R)-enol ((R)-12a) by NaBH4 reduction.Alkaline hydrolysis of (R)-11a and (R)-12a gave (R)-1a and (R)-2a in high yields.Similarly, the (S)-aldehyde ((S)-9) was prepared from (S)-3 and converted to the (12S,15S)-acid ((S)-1a) and (12S,15R)-acid ((S)-2a) by the same sequence of reactions used for the (R)-series.Some (12R,15S)-acid derivatives ((R)-1b-g) with a modified ω-chain were also synthesized.These analogs ((R)-1b-g) were also prepared from (R)-9 via synthetic sequences similar to that described above.Keywords - heterocyclic prostaglandin; (12R,15S)-(-)-11-deoxy-8-azaprostaglandin E1; (12R,15R)-(-)-11-deoxy-8-azaprostaglandin E1; (12S,15S)-(+)-11-deoxy-8-azaprostaglandin E1; (12S,15R)-(+)-11-deoxy-8-azaprostaglandin E1; (R)-(-)-methyl 7-(5-formyl-2-oxo-1-pyrrolidine)heptanoate; (S)-(+)-methyl 7-(5-formyl-2-oxo-1-pyrrolidine)heptanoate

1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones

Certain 1,5-disubstituted 2-pyrrolidinones, and their ring unsaturated analogs, resemble natural prostaglandins. The compounds are easier to prepare than the prostaglandins since they have at least one fewer center of asymmetry and accordingly fewer isomers are produced. Exemplary is 7-[2-oxo-5-(3-hydroxy-1-oct-1-enyl)-1-pyrrolidinyl]heptanoic acid of the formula: SPC1