HCID 20223681, compound → HCID 12397275, compound

Participants

Reaction Steps

Into a 500 ml. Parr bottle there was introduced 13.4 g. (0.04 mole) of 3-hydroxy-6-(1-hydroxy-2-tertbutylaminoethyl)-2-hydroxymethylpyridine N-oxide dihydrochloride and 6.5 g. of 5% palladium on carbon catalyst in 150 ml. of methanol. Under a hydrogen pressure of 43 psi the mixture was shaken at room temperature for two days. The catalyst was removed by filtration under a nitrogen atmosphere followed by removal of the solvent in vacuo to give an oil which was triturated with isopropanol to induce crystallization. Filtration of the resulting solid afforded 3-hydroxy-6-(1-hydroxy-2-tert-butylaminoethyl)-2-methylpyridine dihydrochloride, 10.0 g. (85%) m.p. 226°-228.5° C. (dec.); NMR (DMSO d6)delta 7.80 (q, 2H, pyridyl H), 5.40 (br m, 1H); 3.30 (br m, 2H), 2.60 (s, 3H, 2--CH3) and 1.35 (s, 9H, t-Bn).

Provenance & Evidence