200716-94-5

Basic information

• Product Name: (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester
• Synonyms: (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester
• CAS NO: 200716-94-5
• Molecular Weight: 576.649
• Mol File: 200716-94-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester(200716-94-5)
• EPA Substance Registry System: (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester(200716-94-5)

Safety Data

• Hazardous Substances Data: 200716-94-5(Hazardous Substances Data)

Upstream product

• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 69876-37-5 (S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoate 
• 100-39-0 benzyl bromide 

Downstream Products

• 16709-25-4 (S)-α-methyltryptophan 

Relevant articles and documents

Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in the enantiospecific preparation of α-methyltryptophan: Application in the preparation of carbon-14 labeled PD 145942 and PD 154075

[2R-(2α,3aβ,8aβ)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8 -tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2β,3aα,8aα)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure α-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-α-[14C]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1 -[14C]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[14C]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.