Sodium hydride → HCID 118377815, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(1R,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]ethanol 1m (0.4 g, 0.56 mmol, obtained from the synthetic method described in step 11 of example 1) and chloromethyl pivalate (0.36 mL, 2.5 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (77.8 mg, 1.95 mmol, 60% dispersion in Mineral oil) at 0° C. The mixture was heated to 40° C. and stirred for 48 hours. The resulting mixture was quenched with saturated ammonium chloride (20 mL), and then extracted with ethyl acetate (60 mL×3). The combined organic layers were washed with water (50 mL×2) and then saturated brine (50 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 14a as light yellow oil (125 mg, 27.8%). The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, CDCl3) δ (ppm): 7.42-7.30 (m, 10H), 7.28-7.15 (m, 6H), 7.07 (m, 2H), 6.91 (m, 2H), 6.76 (m, 2H), 5.20 (m, 1H), 4.98 (d, 1H), 4.89-4.82 (m, 2H), 4.31 (m, 1H), 4.25 (d, 1H), 4.11-3.80 (m, 7H), 3.86 (d, 1H), 3.70 (m, 2H), 1.41 (t, 3H), 1.27 (d, 3H), 1.20 (s, 9H).

Provenance & Evidence