86718-70-9

Basic information

• Product Name: (+)-Cisapride
• Synonyms: (+)-cis-Apride;(+)-(R)-Cisapride
• CAS NO: 86718-70-9
• Molecular Formula: C₂₃H₂₉ClFN₃O₄
• Molecular Weight: 0
• Mol File: 86718-70-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Cisapride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Cisapride(86718-70-9)
• EPA Substance Registry System: (+)-Cisapride(86718-70-9)

Safety Data

• Hazardous Substances Data: 86718-70-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Cisapride is used as a prokinetic agent for treating conditions such as gastroesophageal reflux disease (GERD) and gastroparesis, due to its ability to stimulate gastrointestinal muscles and speed up stomach emptying.
Used in Research and Development:
(+)-Cisapride is utilized as a key molecule in the research and development of new drugs targeting the gastrointestinal system, despite its withdrawal from the market due to serious side effects.

Upstream product

• 1345718-94-6 tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate 
• 503433-37-2 C₁₅H₂₃FN₂O₂ 
• 150007-96-8 C₁₁H₁₂ClNO₅ 
• 7206-70-4 4-amino-5-chloro-2-methoxybenzoic acid 
• 1129-78-8 1-(3-bromopropoxy)-4-fluorobenzene 
• 401502-00-9 N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine 
• 1345718-98-0 (3S,4R,αR)-N(1)-(3'-(4''-fluorophenoxy)propyl)-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidine 
• 1345718-97-9 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-methoxy-4-[N-benzyl-N-(α-methylbenzyl)amino]piperidin-2-one 
• 1345718-96-8 (R,R,R)-N(1)-[3'-(4''-fluorophenoxy)propyl]-3-hydroxy-4-[N-benzyl-N-(α-methylbenzyl)amino]-piperidin-2-one 
• 1345718-95-7 tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate 

Downstream Products

• 102671-04-5 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-hydroxy-benzamide 
• 102671-13-6 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-(2-methylsulfanyl-ethoxy)-benzamide 
• 125557-41-7 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-(2-methanesulfinyl-ethoxy)-benzamide 

Relevant articles and documents

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride

The conjugate addition of lithium (R)-N-benzyl-N-(α-methylbenzyl) amide to δ-(N-allylamino)-α,β-unsaturated esters, followed by N-deallylation and cyclisation of the resultant β,δ-diamino esters, gives the corresponding 4-aminopiperidin-2-ones as single diastereoisomers (>99:1 dr). Subsequent deprotonation with LiHMDS and functionalisation of the resultant lithium enolate gives 3,4-anti-3-substituted-4-aminopiperidin-2-ones in >99:1 dr. Alternatively, in situ oxidation of the intermediate lithium (Z)-β-amino enolates formed upon conjugate addition gives α-hydroxy-β,δ-diamino esters, which after N-deallylation and cyclisation gives the corresponding 3,4-syn-3-hydroxy-4-aminopiperidin-2-ones in >99:1 dr. The utility of this methodology was successfully demonstrated in a concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)- cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy)propyl]-3-methoxy- 4-(2?-methoxy-4?-amino-5?-chlorobenzamido)piperidine} in nine steps from commercially available starting materials with an overall yield of 19%.

Concise, efficient and highly selective asymmetric synthesis of (+)-(3S,4R)-cisapride

A concise asymmetric synthesis of the gastroprokinetic agent (+)-(3S,4R)-cisapride {(+)-(3S,4R)-N(1)-[3′-(4″-fluorophenoxy) propyl]-3-methoxy-4-(2″′-methoxy-4″′-amino- 5″′-chlorobenzamido)piperidine} from commercially available starting materials has been developed. The key step of this synthesis employs the diastereoselective conjugate addition of lithium (R)-N-benzyl-N-(α- methylbenzyl)amide to tert-butyl 5-[N-3′-(4″-fluorophenoxy)propyl-N- allylamino]pent-2-enoate and in situ enolate oxidation with (-)- camphorsulfonyloxaziridine to set the (3S,4R)-configuration found within the piperidine ring of the product. This synthesis proceeds in 9 steps from commercially available 1-(4′-fluorophenoxy)-3-bromopropane with an overall yield of 19%.