Trimethylsilyl iodide → HCID 58379622, compound

Participants

Reaction Steps

To a cooled (0° C.) yellow solution of compound 49 (5.0 g, 9.2 mL) in chloroform (130 mL) was added iodotrimethylsilane (TMSI) (9.0 mL, 64 mmol), dropwise, turning to an orange mixture. After 3 hours the reaction was quenched with methanol and concentrated. The resulting residue was slurried in diethyl ether and filtered solids, and the solids were washed with diethyl ether to remove all benzyl iodide. To the solids was then added 2 N sodium hydroxide (20 mL) and water (150 mL). With stirring the orange suspension slowly turned to a cream suspension. The solids were collected by filtration and purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0-10%) to afford Compound 118 (3.6 g, 96%).

Provenance & Evidence