124223-92-3

Basic information

• Product Name: 2,5-Pyrrolidinedione, 3-amino-1-(phenylmethyl)-, (3S)-
• CAS NO: 124223-92-3
• Molecular Formula: C11H12N2O2
• Molecular Weight: 204.228
• Mol File: 124223-92-3.mol

Chemical Properties

• CAS DataBase Reference: 2,5-Pyrrolidinedione, 3-amino-1-(phenylmethyl)-, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedione, 3-amino-1-(phenylmethyl)-, (3S)-(124223-92-3)
• EPA Substance Registry System: 2,5-Pyrrolidinedione, 3-amino-1-(phenylmethyl)-, (3S)-(124223-92-3)

Safety Data

• Hazardous Substances Data: 124223-92-3(Hazardous Substances Data)

Usage

Chemical compound

2,5-Pyrrolidinedione, 3-amino-1-(phenylmethyl)-, (3S)-

Class

Pyrrolidinedione derivatives

Also known as

(3S)-3-amino-1-(phenylmethyl)pyrrolidine-2,5-dione

Chiral molecule

Yes, with a stereocenter at the 3rd carbon atom

Uses

Reagent in organic synthesis and pharmaceutical research

Importance

Used in the development of new drugs and pharmaceutical compounds.

Upstream product

• 100-39-0 benzyl bromide 
• 124166-11-6 (S)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester 

Downstream Products

• 145223-69-4 (S)-1-benzyl-3-(benzylamino)pyrrolidine 
• 145223-77-4 ((S)-1-Benzyl-pyrrolidin-3-yl)-phenethyl-amine 
• 145223-82-1 ((S)-1-Benzyl-pyrrolidin-3-yl)-(4-chloro-benzyl)-amine 
• 145223-80-9 (3S)-1-benzyl-N-(2-naphthylmethyl)pyrrolidin-3-amine 
• 145223-83-2 ((S)-1-Benzyl-pyrrolidin-3-yl)-(4-methoxy-benzyl)-amine 
• 145223-79-6 ((S)-1-Benzyl-pyrrolidin-3-yl)-naphthalen-1-ylmethyl-amine 
• 145223-78-5 (R)-N-Benzyl-N-((S)-1-benzyl-pyrrolidin-3-yl)-2-fluoro-2-phenyl-acetamide 
• 145223-70-7 (S)-N-Benzyl-N-((S)-1-benzyl-pyrrolidin-3-yl)-2-fluoro-2-phenyl-acetamide 
• 114715-38-7 (3S)-1-benzyl-3-pyrrolidinamine 
• 145223-73-0 (S)-1-Benzyl-3-{[1-naphthalen-2-yl-meth-(E)-ylidene]-amino}-pyrrolidine-2,5-dione 
• 145223-76-3 (S)-1-Benzyl-3-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-pyrrolidine-2,5-dione 
• 145223-68-3 (S)-1-Benzyl-3-{[1-phenyl-meth-(E)-ylidene]-amino}-pyrrolidine-2,5-dione 
• 145223-72-9 (S)-1-Benzyl-3-{[1-naphthalen-1-yl-meth-(E)-ylidene]-amino}-pyrrolidine-2,5-dione 
• 145223-75-2 (S)-1-Benzyl-3-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-pyrrolidine-2,5-dione 

Relevant articles and documents

Process for producing 1H-3-aminopyrrolidine and derivatives thereof

A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R'NH2, subjecting the reaction product to cyclodehydration to obtain an optically active 1-aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

Process for producing 1H-3-aminopyrrolidine and derivatives thereof

A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino

Methods for making optically active 3-aminopyrrolidine-2,5-dione derivative and optically active 3-aminopyrrolidine derivative

A method for making an optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) includes cyclizing an optically active asparagine ester derivative represented by the formula (1) or (2) or an acid salt thereof. The optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) may be reduced to form an optically active 3-aminopyrrolidine derivative represented by the formula (9). When, in the formula (9), R1 is an unsubstituted or substituted benzyl group, the compound may be hydrogenated to obtain the corresponding 1-unsubstituted compound in which R1 is hydrogen.

Methods for making optically active 3-aminopyrrolidine-2,5-dione derivative and optically active 3-aminopyrrolidine derivative

A method for making an optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) includes cyclizing an optically active asparagine ester derivative represented by the formula (1) or (2), or an acid salt thereof. A method for making an optically active 3-aminopyrrolidine derivative represented by the formula (9) includes reducing the optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3). A method for making an optically active 3-aminopyrrolidine derivative includes hydrogenolyzing the optically active 3-aminopyrrolidine derivative represented by the formula (9).

Handy access to chiral N,N'-disubstituted 3-aminopyrrolidines

A new and rapid synthesis of (S)-3-aminopyrrolidines Z is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the