HCID 117929159, compound → HCID 118377853, compound

Participants

Reaction Steps

To a solution of (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carbaldehyde 19b (3 g, 4.15 mmol) in dry tetrahydrofuran (50 mL) was added methylmagnesium bromide (2 mL, 6.22 mmol, 3M in ethyl ether) dropwise at 0° C. The mixture warmed up to room temperature and stirred for 5 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (10 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with water (50 mL×2) and then saturated aqueous sodium chloride (50 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 19c as yellow oil (2.16 g, 70.4%).

Provenance & Evidence