tert-Butanol → 3'-(Pyridin-4-ylmethoxy)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added 3′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (7.89 g, 26.4 mmol, 1.0 eq.), pyridin-4-yl-methanol (3.74 g, 34.3 mmol, 1.3 eq) and 1M potassium tert-butyl butoxide in t-butanol (72 ml, 72 mmol, 2.7 eq). The reaction was then stirred overnight at room temperature after which the solvent was removed. The solid was then diluted with EtOAc, washed 3× with water, 2×NaHCO3, 2× with brine, and dried over NaSO4. Purification was then accomplished on column chromatography with the eluent being 1:2 ethyl acetate/hexane and 2% TEA. Removal of the solvent resulted in the title compound as a cream solid (6.98 g, 33% yield).

Provenance & Evidence