Lithium Hydroxide → HCID 178525542, compound

Participants

Reaction Steps

A round bottom flask was charged with the product from Example 26B (0.520 g, 1.36 mmol) and 6 mL of 20% aqueous tetrahydrofuran. Lithium hydroxide was added (114 mg, 2.72 mmol), and the reaction stirred at room temperature overnight. After 16 hours, the reaction was quenched with 1 N HCl, and the mixture filtered over a bed of celite. Evaporation of the solvents and purification via silica gel chromatography (10-30% ethyl acetate/hexanes with 1% acetic acid) afforded the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.04-1.23 (m, 2 H), 1.41-1.57 (m, 2 H), 1.58-1.67 (m, 1 H), 1.69-1.77 (m, 1 H), 1.78-1.88 (m, 4 H), 2.12-2.20 (m, 2 H), 7.05-7.17 (m, 1 H), 7.26-7.41 (m, 2 H), 7.62-7.82 (m, 2 H), 12.00 (s, 1 H), 13.89-14.07 (m, 1 H); MS (ESI) m/z 354 [M+H]+.

Provenance & Evidence