Water → HCID 23001825, compound

Participants

Reaction Steps

A solution of Sml2 in THF (0.1 M, 21.9 mL, 2.19 mmol) was added to a solution of the alkene of Example 50 (194 mg, 0.55 mmol) in THF (5 mL) under nitrogen followed by water (1 mL). After stirring at room temperature for 10 min the reaction was quenched with 6M NaOH (10 mL) and stirred for 30 min. The organic phase was separated and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were dried (MgSO4) and evaporated to an oil, which was purified by column chromatography [SiO2; 93:7:1 (DCM/MeOH/880 NH3) increasing polarity to 90:10:1] to give the title compound (90 mg, 46%); δH (CDCl3, 400 MHz) 2.25 (6H, s), 2.54 (2H, t), 2.97 (2H, t), 3.22 (2H, t), 3.36 (2H, t), 3.42 (2H, s), 5.20-5.46 (2H, br), 6.54 (1H, d), 6.73 (1H, s), 6.81 (1H, d), 7.05 (2H, m), 7.31 (1H, s); MS m/z (TS+) 357 (MH+).

Provenance & Evidence