(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane → Tetrazolo[1,5-a]pyridine-6-methanol

Participants

Reaction Steps

A solution of 725 mg (3.55 mmol) of (1,1-dimethyl-2-(5-hydroxy-1H-indol-3-yl))ethyl amine (R. V. Heinzelman, et al., J. Org. Chem., 25, 1548 (1960)) and 598 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane in 15 ml of absolute ethanol was stirred at reflux under nitrogen for 13 hours. The reaction mixture was concentrated under reduced pressure to give 1.05 g of crude product. This material was chromatographed on silica gel (90:10:1 CH2Cl2 :MeOH:NH4OH) to give 927 mg of partially purified material. Preparative TLC on silica gel in the same solvent system (eluted twice) afforded pure (R)-α-[[(1,1-dimethyl-2-(5-hydroxy-1H-indol-3-yl))ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol (741 mg).

Provenance & Evidence