Indole-3-carboxylic acid, 1-methoxy methyl ester

Esters of 2-(2-azidophenyl)ethyl alcohol are photolyzed under a high-pressure mercury lamp to a reactive nitrene intermediate which, following insertion into the alkyl side-chain, undergoes elimination to give the free carboxylic acid (up to 32%) and producing indole. The photochemical release was somewhat improved (65-80%) when 5-azido-4-(hydroxy-methyl)-l-methoxy naphthalene was used (see Scheme 27). 

To a solution of the S-(+)-4-acethoxy-9-[2-(5-ethyl-l,2,3,6-tetrahydro-pyridin-3yl)-l-(lH-indol-2-yl)-l-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,ll,12,12b-octahydro-lH-6,12a-diaza-indeno[7,l-ca]fluorene-5-carboxylic acid methyl ester in dioxane and glacial acetic acid was added 37% aqueous formaldehyde and the mixture stirred at 35°C for 24 h. The solution was evaporated in vacuo and the residue suspended in chloroform and washed with cold aqueous 5% K2C03 solution. The chloroform layer was dried (MgS04), filtered, and evaporated. The residue was chromatographed eluting with EtOAc/MeOH, 10% NH4OH to give the product navelbine. 

C111H15N3O5 0.5 CH4O, 3-Carbamoyl-1,2-dihydro-4-hydroxy-5-methoxy-3H-pyrrolo[3,2-e]indole-7-carboxylic acid methyl ester methanol solvate, 44B, 255... 

CA Index Name l//-Indole-6-carboxylic acid, 2-[4-[bis [2- [(acetyloxy)methoxy] -2-oxoethyl] amino] -3- [2- [2-[bis[2-[(acetyloxy)methoxy]-2-oxoethyl]amino]-5-me-thylphenoxyjethoxyjphenyl]-, (acetyloxy)methyl ester... 

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