Triethylamine → HCID 117986053, compound

Participants

Reaction Steps

To a solution of (1R,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(1-hydroxyethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 1 (10.0 g, 21.6 mmol, HPLC: 97.5%) in methanol (80 mL) were added Pd/C (1.5 g, 0.705 mmol, 5%) and triethylamine (5 mL, 32.4 mmol) at room temperature in turn. The mixture was stirred at room temperature under H2 for 20 hours and filtered. The filtrate was concentrated in vacuo. To the residue were added ethyl acetate (80 mL) and water (50 mL) and the resulting mixture was stirred at room temperature for 5 min, then stood for a few minutes and partitioned. The organic layer was washed with saturated aqueous sodium chloride (50 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 30 as a white solid (9.2 g, 99.6%, HPLC: 97.1%). The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, CD3OD) δ (ppm): 7.43 (s, 1H), 7.38 (d, 1H), 7.26 (t, 1H), 7.15 (d, 1H), 7.11 (d, 2H), 6.82 (d, 2H), 4.18 (d, 1H), 4.01 (m, 3H), 3.95-3.91 (m, 3H), 3.80 (dd, 1H), 3.68 (t, 1H), 3.60 (d, 1H), 1.37 (t, 3H), 1.33 (d, 3H); and MS (ESI, pos. ion) m/z: 417.1[M+H]+.

Provenance & Evidence