Trifluoroacetic acid → HCID 21706317, compound

Participants

Reaction Steps

To the product (1 g, 1.94 mmol) of Example 28 dissolved in anhydrous THF (80 mL) was added LAH (0.47 g, 12.4 mmol) at 0-5° C. under nitrogen. The reaction mixture was stirred for 2 hours and quenched with ice-cold NaOH (0.5 M) solution. The organic layer was extracted with ethyl acetate, combined, dried and concentrated in vacuo. To this residue (0.88 g, 1.8 mmol) dissolved in dichloromethane (˜50 mL) was added triethylsilane (1.73 mL, 10.8 mmol) and TFA (0.42 mL, 5.4 mmol). The reaction mixture was stirred for 1.5 hours before it was washed with dilute NaOH solution and brine until neutral. The combined organic layers were dried with Na2SO4 and concentrated. The residue was purified by column chromatography (20% CH3OH in dichloromethane) to yield 0.53 g (63%) of title compound.

Provenance & Evidence