183866-63-9

Basic information

• Product Name: (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate
• Synonyms: (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate
• CAS NO: 183866-63-9
• Molecular Weight: 317.385
• Mol File: 183866-63-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate(183866-63-9)
• EPA Substance Registry System: (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate(183866-63-9)

Safety Data

• Hazardous Substances Data: 183866-63-9(Hazardous Substances Data)

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 183866-61-7 5-((R)-1-Hydroxy-ethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 72504-66-6 (1R)-1-(1-benzyl-1,2,5,6-tetrahydro-3-pyridyl)ethanol 
• 501-53-1 benzyl chloroformate 
• 350-03-8 methyl-3-pyridylketone 
• 4754-27-2 1-(3-Pyridyl)ethanol 
• 5096-11-7 (R)-1-(3-pyridyl)ethanol 
• 27854-86-0 (1R)-1-(3-pyridyl)ethyl acetate 

Downstream Products

• 6474-90-4 tetrahydroalstonine 
• 483-04-5 ajmalicine 
• 183866-66-2 (R)-3-Eth-(Z)-ylidene-4-(1H-indol-2-ylmethyl)-piperidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

ENANTIOSELECTIVE SYNTHESES OF HETEROYOHIMBINE NATURAL PRODUCT INTERMEDIATES

Enantioselective syntheses of cis- and trans-bicyclic dihydropyran compounds, and other intermediates, en route to heteroyohimbine alkaloids.

Total syntheses of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20-dihydroakuammicine

Two different strategies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of 1-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally Smith indolization. Whereas 2-(4-piperidylmethyl)indole 6 could not be converted to tetracyclic ABDE substructures of Strychnas alkaloids, photocyclization of chloroacetamide 14, derived from (piperidylmethyl)indole 13, satisfactorily afforded the stemmadenine-type tetracycle 15, which was then converted to the alkaloids (-)-tubifoline, (-)-tubifolidine, and (-19,20-dihydroakuammicine.