Sodium borohydride → HCID 57595182, compound

Participants

Reaction Steps

A 100 mL round bottom flask was charged with oxazolidine 41 (1.65 g, 3.91 mmol), ethanol (50 mL), and sodium borohydride (450 mg, 11.9 mmol), and stirred at room temperature for 3 hours. The reaction was then quenched with 16 mL of a 20% NH4Cl aqueous solution and concentrated under reduced pressure, then diluted with water and neutralized with an aqueous solution of potassium carbonate. The solution was then extracted with methylene chloride (3×50 mL). The organic extracts were then pooled, dried over MgSO4, filtered and concentrated under reduced pressure to give (dimethylamino)ethanol 42 (crude yield: 1.31 g, 78%). The crude product was then dissolved in a minimum volume of CH2Cl2, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 42: 1.01 g (60% over two steps). 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 6H), 2.49 (m, 2H), 2.58 (s, 3H), 4.77 (m, 1H), 5.40 (bs, 1H), 6.86 (d, J=5.6 Hz, 1H), 7.16 (dd, J=7.2, 1.6 Hz, 1H), 7.29 (t, J=8.8 Hz, 2H), 7.64 (m, 3H), 8.45 (d, J=5.6 Hz, 1H), 9.32 (d, J=7.2 Hz, 1H). MS (ESI+) 424.2.

Provenance & Evidence