Tetrahydrofuran → HCID 66686029, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 2,2-dimethyl-4-oxo-4-phenylbutanoate from Step A (0.51 g, 2.3 mmol) and 2-methylpropane-2-sulfinamide (0.34 g, 2.8 mmol) in THF (12 mL) was added titanium tetraethoxide (1.4 g, 5.6 mmol). This mixture was then heated to 60° C. for 3 days. After cooling to 0° C. in an ice bath, sodium borohydride (0.18 g, 4.7 mmol) was added. Following 90 minutes of stirring at 0° C., MeOH was added slowly (drop-wise) until hydrogen gas evolution ceased. Next, saturated brine (˜12 mL) was added, with vigorous stirring. The resulting mixture was filtered through celite using copious amounts of EtOAc. This organic filtrate was washed with saturated brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of EtOAc:Hexane—10:90 to 70:30, to give the title compound. MS: m/z=340 (M+1).

Provenance & Evidence