Formaldehyde → HCID 89662849, compound

Participants

Reaction Steps

A mixture of Example 104 (112 mg; 0.25 mmol; 1 eq.), paraformaldehyde (68 mg; 0.76 mmol; 3.00 eq.) and sodium triacetoxyborohydride (107 mg; 0.50 mmol; 2 eq.) in DCE (5 mL) was stirred at reflux for 2 hours. 1M NaOH was added and extracted several times with EtOAc. The combined organics were dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (22 mg, 21%) as a white solid. 1H NMR (CDCl3) δ 7.40-7.33 (m, 2H), 7.11-7.05 (m, 1H), 6.73-6.69 (m, 1H), 5.03-5.01 (m, 2H), 4.97-4.89 (m, 1H), 4.61-4.60 (m, 2H), 4.16-4.10 (m, 2H), 3.34-3.28 (m, 2H), 2.91 (s, 2H), 2.85 (s, 1H), 2.69 (s, 1H), 2.62 (s, 2H), 2.51 (s, 3H). HPLC (max plot) 98%, Rt 1.92 min. UPLC/MS: (MS+) 412.4 ([M+H]+).

Provenance & Evidence