1027058-54-3

Upstream product

• 200716-92-3 (2R,3aS,8aS)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester 
• 2279-15-4 N-(benzyloxycarbonyl)-D-tryptophan 
• 200716-91-2 (2R,3aS,8aR)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester 
• 200716-90-1 (2R,3aS,8aS)-3,3a,8,8a-Tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dibenzyl ester 
• 126496-81-9 (R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 56452-52-9 α-methyl-DL-tryptophan 

Relevant academic research and scientific papers

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.