Acetic Acid → HCID 89662755, compound

Participants

Reaction Steps

A mixture of Example 100 (98 mg; 0.22 mmol; 1 eq.), acetone (95 μL; 1.3 mmol; 6 eq.), sodium triacetoxyborohydride (183 mg; 0.86 mmol; 4 eq.) and AcOH (15 μL; 0.26 mmol; 1 eq.) in DCE (5 mL) was stirred at room temperature for 16 hours. Acetone (95 μL; 1.3 mmol; 6 eq.), sodium triacetoxyborohydride (183 mg; 0.86 mmol; 4 eq.) and AcOH (15 μL; 0.26 mmol; 1 eq.) were added and the resulting mixture was stirred at room temperature for 24 hours. 1M NaOH was added and the two phases separated. The aqueous layer was extracted with DCM (2×). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (5% to 20% MeOH in DCM) afforded the title compound (78 mg, 72%) as a colourless oil. 1H NMR (DMSO-d6) δ 7.44-7.33 (m, 1H), 7.24 (dd, J=7.4, 1.7 Hz, 1H), 7.18-7.09 (m, 1H), 7.00 (t, J=7.4 Hz, 1H), 4.61-4.42 (m, 2H), 4.42-4.27 (m, 1H), 2.83 (s, 3H), 2.63-2.52 (m, 4H), 2.36-2.21 (m, 2H), 1.98-1.74 (m, 8H), 1.68-1.44 (m, 2H), 0.79 (d, J=6.2 Hz, 6H). HPLC (max plot) 86.3%, Rt 3.27 min. UPLC/MS: (MS+) 496.5 ([M+H]+).

Provenance & Evidence