Potassium Hydroxide → HCID 54331189, compound

Participants

Reaction Steps

To a stirred solution of N-benzyl-1-cyano-N-methyl-1-[(R)-3-(1-methyl-2-pyrrolidinylmethyl)-1-trimethylsilylethyloxymethyl-1H-indol-5-yl]methanesulfonamide (from step (b), 1.56 g, 2.8 mmol) in ethanol (12 ml) at ambient temperature was added 2N potassium hydroxide solution (6.24 ml, 12.5 mmol). The dark brown solution was then brought to reflux and maintained at this temperature for 15 hr. The oily reaction mixture was then cooled to ambient temperature and extracted with ethyl acetate (3×25 ml). The organic extracts were combined and evaporated in vacuo to yield the crude product as a dark brown oil. This was purified by flash column chromatography (ethyl acetate:hexane:dietiylamine 1:1:0.1 as eluant) to yield the title compound (1.49 g, 75%) as a brown oil.

Provenance & Evidence