MK 886 → 3-[1-(p-Chlorobenzyl)-3-(t-butylthio)-5-(i-propyl)-indole-2-yl]-2,2-dimethylpropanol

Participants

Reaction Steps

To a solution of 200 mg of methyl 1-(p-chlorobenzyl) -3-(t-butylthio)-α,α-dimethyl -5-(i-propyl)-indole-2-propanoate (from Example 25) in 1.5 mL tetrahydrofuran (THF) was added 0.4 ml of a solution of lithium aluminum hydride (1.0M in THF) at 0° C. After 2 h at 0° C., the reaction mixture was quenched with saturated aqueous Na2SO4, diluted with ether and stirred at room temperature for 1 h. The resultant slurry was filtered and the filtrate concentrated to dryness. The resultant oil was purified by flash chromatography (eluant: hexane ethyl acetate, 8:2) to give the title compound as a viscous oil.

Provenance & Evidence