Tetrahydrofuran → HCID 68863511, compound

Participants

Reaction Steps

A solution of Example 173C (0.21 g, 0.62 mmol) in THF (8 mL) and water (1 mL) was treated with N-methylmorpholine oxide (0.11 g, 0.95 mmol) in one portion and dropwise with OsO4 (2.5% wt solution in tert-butanol, 0.5 mL). The mixture was stirred at room temperature for 4 hours, treated with water (20 mL), followed by 5% aqueous NaHCO3 (10 mL), and extracted with diethyl ether (2×10 mL). The aqueous solution was adjusted to pH 2.0 with 1N HCl and extracted with ethyl acetate (3×10 mL). The combined extracts were dried (MgSO4) filtered, and concentrated to provide the desired product (101 mg, 43.5%). 1H NMR (DMSO-d6) δ 2.22 (s, 3H), 4.73 (m, 2H), 5.18 (m, 1H), 6.79 (d, 1H), 7.34 (d, 1H), 7.40 (m, 2H), 7.80 (m, 2H), 9.80 (br s, 1H), 12.90 (br s, 1H); MS (ESI(−)) m/e 368 (M−H)−.

Provenance & Evidence