60702-96-7

Basic information

• Product Name: 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid
• Synonyms: 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid
• CAS NO: 60702-96-7
• Molecular Weight: 406.481
• Mol File: 60702-96-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid(60702-96-7)
• EPA Substance Registry System: 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid(60702-96-7)

Safety Data

• Hazardous Substances Data: 60702-96-7(Hazardous Substances Data)

Upstream product

• 328-50-7 α-ketoglutaric acid 
• 19779-76-1 (+/-)-N_a-methyl-N_b-benzyltriptophan methyl ester 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 19779-77-2 (+/-)-N_a-methyl-N_b-benzyltriptophan methyl ester hydrochloride 
• 188067-60-9 (R)-methyl 2-amino-3-(1-methyl-1H-indol-3-yl)propanoate 
• 19779-74-9 (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 
• 7638-53-1 N_a-methyl tryptophan methyl ester 
• 100-52-7 benzaldehyde 

Downstream Products

• 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 
• 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 
• 2738-25-2 methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate 
• 22282-00-4 (+/)-5-Methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 122490-92-0 5-methyl-9-hydroxy-9α-chloro-phenylsulfinylmethyl-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 122490-83-9 2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole 
• 141804-40-2 5-methyl-9-butyryloxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 122490-84-0 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 122490-85-1 5-methyl-9-hydroxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 4837-58-5 trans-2-benzyl-3-carboxy-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 

Relevant articles and documents

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.

Selenium Dioxide Oxidations in the Indole Area. Synthesis of β-Carboline Alkaloids

A number of different piperidoindole systems have been subjected to oxidation with selenium dioxide.The bonding between the indole and piperidine unit has been varied to provide different systems, the oxidation of which has led to formation of either 2-acyl- or 3-acylindoles or fully aromatic β-carbolines, depending on the substrate chosen.The pattern of reactivity observed was in complete agreement with the ene mechanism proposed for selenium dioxide oxidations, and this can be employed to predict the regiochemistry of the oxidation.Use of this technology has resulted in a two-step synthesis of the indole alkaloid canthin-6-one (30a).