Chlorotrimethylsilane → HCID 11851783, compound

Participants

Reaction Steps

To a solution of 53 mg (0.100 mmol) 3-7 in 0.75 mL anhydrous THF at −78° C. under N2 was added 60 μL (0.150 mmol) 2.5 M n-BuLi in hexanes dropwise. Immediately following this addition, 51 μL (0.400 mmol) chlorotrimethylsilane was added, the cooling bath was removed, and the reaction warmed to room temperature. After 30 min the reaction was quenched with saturated aqueous NH4Cl solution and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic phase was washed with water, brine, dried with Na2SO4 and concentrated. The residue was purified by reverse-phase preparatory HPLC with CH3CN/H2O (with 0.1% TFA). The fractions containing the desired product were poured into saturated aqueous NaHCO3 solution and extracted with EtOAc and concentrated to yield the freebase 3-8 as a clear, colorless oil.

Provenance & Evidence