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

Participants

Reaction Steps

A solution of 553 mg of partially resolved (R)-1-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl amine (R. A. Glennor et al, Biol Psychiatry, 18,493 (1983) and 452 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane in 10 ml of methanol under nitrogen was heated at reflux for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue (1.0 g) purified by careful preparative TLC on silica gel (95:5:0.5 CH2Cl2 :MeOH:NH4OH) to give 515 mg of (R)-α-[[(1(R)-methyl-2-(5-methoxy-1H-indol-3-yl)ethyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol plus 11.6 mg of the adduct resulting from the small amount of (S)-amine present in the starting material.

Provenance & Evidence