Lithium Hexamethyldisilazide → HCID 118590475, compound

Participants

Reaction Steps

(S,Z)—N-(4-chloro-1-(5-fluoro-2-(((R)-tetrahydrofuran-3-yl)oxy)phenyl)butylidene)-2-methylpropane-2-sulfinamide (7.6 g, 19.5 mmol) in THF (100 mL) was cooled to −78° C. and to which was added cold (−78° C.) Lithium triethylborohydride (1M in THF) (21.48 ml, 21.5 mmol) drop wise and stirring was continued at −78° C. for 3 h. LiHMDS (1M in THF) (19.53 ml, 19.5 mmol) was then added and stirring was continued at −78° C. to 0° C. for 2 h. The resultant reaction mixture was quenched with saturated NH4Cl solution, diluted with ethyl acetate. The ethyl acetate layer separated was washed with water followed by brine solution, dried over anhydrous sodium sulphate and concentrated under reduce pressure to afford the crude residue. The residue thus obtained was purified by column chromatography twice (using initially with 60-120 silica gel and 15% EtOAc in Hexane as elute and again with 230-400 silica gel and 12-14% EtOAc in Hexane as elute) to afford 4.1 g of the title compound as crude, which was used as such for the next step.

Provenance & Evidence