Acetic Acid → HCID 71610203, compound

Participants

Reaction Steps

To a solution of Example 3 (100 mg; 0.23 mmol; 1 eq.) in DCM (3 mL) was added acetone (52 μL; 0.70 mmol; 3 eq.) and AcOH (16 μL; 0.28 mmol; 1.2 eq.) and then after few minutes sodium triacetoxyborohydride (149 mg; 0.70 mmol; 3 eq.). The reaction mixture was stirred at room temperature for 60 hours and acetone (104 μL; 1.41 mmol; 6 eq.) and sodium triacetoxyborohydride (50 mg; 0.23 mmol; 1 eq.). The reaction mixture was stirred for 5 hours then diluted with DCM. The organic phase was washed with sat. aq. NaHCO3, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (45 mg, 41%). 1H NMR (CDCl3) δ 7.41-7.33 (m, 2H), 7.08-6.96 (m, 2H), 4.99 (s, 0.8H), 4.98 (s, 1.2H), 4.66-4.49 (m, 3H), 2.98-2.14 (m, 5H), 2.91 (s, 2H), 2.86 (s, 1H), 2.70 (s, 1H), 2.62 (s, 2H), 1.89-1.61 (m, 4H), 1.09 (s, 6H). HPLC (max plot) 93.8%; Rt 2.80 min. UPLC/MS: (MS+) 468.5 ([M+H]+).

Provenance & Evidence