19779-74-9

Basic information

• Product Name: (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester
• Synonyms: (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester
• CAS NO: 19779-74-9
• Molecular Weight: 320.391
• Mol File: 19779-74-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester(19779-74-9)
• EPA Substance Registry System: (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester(19779-74-9)

Safety Data

• Hazardous Substances Data: 19779-74-9(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 188067-60-9 (R)-methyl 2-amino-3-(1-methyl-1H-indol-3-yl)propanoate 

Downstream Products

• 60702-96-7 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 2738-25-2 (6R,10R)-(+)-methyl-5-methyl-9-oxo-12-benzyl-6,7,8,9,10-hexahydro-6,10-imine-5H-cyclooctindole-8-carboxylate 
• 2738-25-2 (6S,10S)-(-)-methyl-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate 
• 302356-98-5 (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 119980-65-3 1-methyl-2-(3-methoxycarbonylpropan-1-methoxy-1-yl)-3-(R)-<1-(benzylamine)-1-(methoxycarbonylethan-2-yl)>indole 
• 119980-66-4 1-methyl-2-(E)-(3-methoxycarbonylpropyl-1-en-1-yl)-3-(R)-<1-(benzylamine)-1-(methoxycarbonylethan-2-yl)>indole 
• 84129-60-2 trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 120056-44-2 cis-(1R,3R)-(+)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 123806-87-1 (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole 
• 120053-66-9 D-(+)-N_a-methyl-N_b-benzyltryptophan methyl ester 
• 210552-30-0 C₃₀H₃₆N₂O 
• 210552-31-1 C₃₂H₄₀N₂O₂ 
• 143065-07-0 (-)-(6S,8S,9S,10S,1'R)-5-methyl-8-(1'-ethyl-2'-oxoethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole 
• 143065-03-6 (6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole 

Relevant articles and documents

General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction

A general approach (oxyanion-Cope strategy) for the synthesis of sarpagine/ajmaline indole alkaloids has been developed. (+)-Ajmaline 1 and alkaloid G 2 as well as norsuaveoline 3 have been synthesized from D-(+)-tryptophan in enantiospecific fashion via

STEREOSPECIFICITY IN THE PICTET-SPENGLER REACTION. ENANTIOSPECIFIC SYNTHESIS OF (6S,10S)-(-)-5-METHYL-9-OXO-12-BENZYL-6,7,8,9,10,11-HEXAHYDRO-6,10-IMINO-5H-CYCLOOCTINDOLE, A TEMPLATE FOR PREPARATION OF MACROLINE/SARPAGINE ALKALOIDS

The synthesis of the tetracyclic ketone was carried out in enantiospecific fashion (>98percent ee) via the 1,3-transfer of chirality from Na-methyl, Nb-benzyl tryptophan methyl ester to the trans diastereomer in the Pictet-Spengler reaction.Although the condensation of 14 with aldehyde (15) in refluxing benzene generated the tetrahydro β-carbolines (4b/5b) in a kinetic ratio (72:28), epimerization (C-1) of the cis diastereomer into the trans isomer occurred stereospecifically under acidic conditions.Dieckmann cyclizatin of either the Na-methyl, Nb-benzyl-cis-(+)-5b or trans-(-)-4b diastereomer provided the cis-bicyclo-azanonane system at approximately the same rate, although the β-keto esters were antipodal, in contrast to results reported in the Na-benzyl series by Magnus.