Lithium tri-s-butylborohydride → 2-[[(1R,2S,4R,5R)-5-hydroxy-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-isopropyl-5-methyl-2-((1R,2S,4R)-5-oxobicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one (0.380 g, 1.36 mmol) in anhydrous THF (20 mL) was added L-Selectride (1.0 M solution in THF, 4.07 mL, 4.07 mmol) in anhydrous THF at −78° C. under nitrogen. After stirring at −78° C. for 3 h., the reaction was quenched with hydrogen peroxide (35 wt % solution in water, 4 mL) and NaOH (10% aqueous, 7 mL). The mixture was warmed to ambient temp. and then in a 65° C. bath overnight. The volatiles were removed in vacuo. The residue was partitioned between CHCl3/i-PrOH (v/v=3/1) and brine. The organic portion was separated, dried over MgSO4, filtered, and conc. in vacuo. The residue was purified by flash column chromatography (0 to 5% of MeOH in EtOAc) to give the title compound as a white solid.

Provenance & Evidence