1-(1H-indol-3-yl)-2-methylpropan-2-amine → (R)-alpha-[[(1,1-dimethyl-2-(1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol

Participants

Reaction Steps

A solution of 670 mg (3.58 mmol) of (1,1-dimethyl-2-(1H-indol-3-yl)ethyl amine (B. Heath-Brown and P. G. Philpott, J. Chem. Soc., 7165 (1965)) and 598 mg (3.69 mmol) of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane in 12 ml of absolute ethanol was heated at reflux for 15 hours. The reaction mixture was concentrated and the residue (1.24 g) chromatographed on silica gel (95:5:1 CH2Cl2 :MeOH:conc. NH4OH) to give 808 mg of (R)-α-[[(1,1-dimethyl-2-(1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Provenance & Evidence