256464-76-3

Basic information

• Product Name: 2-Pyrrolidinemethanol,4-amino-1-ethyl-,(2R,4S)-(9CI)
• Synonyms: 2-Pyrrolidinemethanol,4-amino-1-ethyl-,(2R,4S)-(9CI)
• CAS NO: 256464-76-3
• Molecular Formula: C7H16N2O
• Molecular Weight: 144.21
• Product Categories: AMINETERTIARY
• Mol File: 256464-76-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Pyrrolidinemethanol,4-amino-1-ethyl-,(2R,4S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinemethanol,4-amino-1-ethyl-,(2R,4S)-(9CI)(256464-76-3)
• EPA Substance Registry System: 2-Pyrrolidinemethanol,4-amino-1-ethyl-,(2R,4S)-(9CI)(256464-76-3)

Safety Data

• Hazardous Substances Data: 256464-76-3(Hazardous Substances Data)

Upstream product

• 142292-42-0 (2S,4R)-4-azido 2-ethoxycarbonyl-N-ethyl pyrrolidine 
• 33996-30-4 trans-4-hydroxy-L-proline ethyl ester hydrochloride 
• 140161-13-3 N-ethyl-4-hydroxy-(S)-prolineethyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 1026437-21-7 (2S,4S)-4-Chloro-1-ethyl-pyrrolidine-2-carboxylic acid ethyl ester 
• 142292-36-2 (2S,4S)-4-azido-2-ethoxycarbonylN-ethyl pyrrolidine 
• 142292-35-1 (2S,4R)-2-ethoxycarbonyl-N-ethyl-4-methanesulfonyloxy pyrrolidine 
• 142292-40-8 (2R,4R)-4-azido-2-ethoxycarbonyl-N-ethyl pyrrolidine 
• 77449-99-1 (2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 142228-42-0 (2R,4R)-1-Ethyl-4-hydroxy-pyrrolidine-2-carboxylic acid ethyl ester 
• 142292-43-1 (2R,4S)-4-azido-2-ethoxycarbonyl-N-ethyl pyrrolidine 

Relevant articles and documents

Synthesis and pharmacological activity of 4-amino-5-chloro-2-methoxy-N- [(2S,4S)-1-ethyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide (TKS159) and its optical isomers

Of 4-amino-5-chloro-2-methoxy-N-(1-ethyl-2-hydroxymethyl-4- pyrrolidinyl)benzamide, four optical isomers, (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, were prepared from optically active 4-amino-1- ethyl-2-hydroxymethylpyrrolidine di-p-toluenesulfonate [(2S,4S)-14, (2S,4R)- 17, (2R,4S)-20 and (2R,4R)-23, respectively]. The requisites, (2S,4S)-14, (2S,4R)-17, (2R,4S)-20 and (2R,4R)-23, were prepared from a commercially available trans-4-hydroxy-L-proline. The absolute configurations of (2S,4S)-1 (TKS159), (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27 were spectroscopically determined. Of the benzamide derivatives, four optical isomers, (2S,4S)-1, (2S,4R)-25, (2R,4S)-26 and (2R,4R)-27, showed a relatively potent affinity for 5-hydroxytryptamine 4 (5-HT4) receptors in a radioligand binding assay ([3H]GR113808). The activities of 25 - 27 were less effective than that of 1 for the gastric emptying of a phenol red semisolid meal in rats. All this suggests that the most potent of the isomers was 4-amino-5-chloro-2-methoxy- N-[(2S,4S)-1-ethyl-2-hydroxymethyl-4-pyrrolidinyl]benzamide (1).