5-METHOXY-alpha,alpha-DIMETHYL-1H-INDOL-3-YL-ETHANEAMINE → (R)-alpha-[[(1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol

Participants

Reaction Steps

A solution of 598 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane and 782 mg of (1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl amine (B. Heath-Brown and P. G. Philpott, J. Chem. Soc., 7165 (1965)) in 12 ml of absolute ethanol was heated at reflux for 44 hours. The reaction mixture was concentrated and the residue (1.15 g) was chromatographed on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 0.997 g of (R)-α-[[(1,1-dimethyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Provenance & Evidence