Acetone → HCID 11501747, compound

Participants

Reaction Steps

To a solution of 1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-5-(methylsulfonyl)-1H-benzimidazole (Example 4, 67 mg, 0.21 mmol) in tetrahydrofuran was added lithium bis(trimethylsilyl)amide (1.06 M in hexane, 217 μL, 0.23 mmol) at −40° C. under nitrogen atmosphere. After stirring for 5 min, excess acetone was added at −40° C. and the mixture was allowed to warm to room temperature. After stirring for 18 h, the mixture was quenched with saturated ammonium chloride aqueous solution and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by PTLC (hexane:ethyl acetate=1:1, three times) to afford the title compound (6.4 mg, 8%) as a white amorphous solid.

Provenance & Evidence