Ammonium Hydroxide → HCID 118377849, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(oxiran-2-yl)-6,8-dioxabicyclo[3.2.1]octane 10a (0.4 g, 0.56 mmol) in a methanol/tetrahydrofuran mixture (v/v=1/2, 9 mL) was added ammonium hydroxide (2 mL, 10 mmol). The mixture was heated to 55° C. and stirred for 16 hours. The resulting mixture was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with water (30 mL×2) and saturated brine (30 mL×2) in turn, 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)=6/1 to give the title compound 10b as colourless oil (0.21 g, 51.2%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.48 (m, 2H), 7.40 (m, 1H), 7.33 (m, 4H), 7.26 (m, 6H), 7.18 (m, 3H), 7.05 (m, 2H), 7.04 (m, 2H), 6.85 (m, 2H), 4.90 (m, 1H), 4.77 (m, 3H), 4.26 (d, 1H), 4.11 (d, 2H), 4.00 (m, 2H), 3.91 (m, 3H), 3.85 (t, 1H), 3.71 (m, 4H), 2.71 (m, 1H), 2.56 (m, 1H), 1.26 (t, 3H).

Provenance & Evidence