Triacetoxyperiodinane → (S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-formyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

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Reaction Steps

To a solution of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(hydroxymethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.2747 g, 0.579 mmol) in wet DCM (5 mL) was added Dess-Martin periodinane (0.319 g, 0.752 mmol) and the mixture was stirred at room temperature. After 3 h, the solids were removed by filtration. The filtrate was washed with aq Na2S2O3, dried (Na2SO4), filtered and concentrated. The resulting oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give the title compound (0.1962 g, 0.415 mmol, 71.7% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.17 (s, 1H), 7.02 (s, 1H), 6.19-5.98 (m, 1H), 5.96-5.76 (m, 1H), 5.57-5.37 (m, 2H), 5.24 (dd, J=10.4, 1.6 Hz, 1H), 4.24 (dd, J=15.9, 7.1 Hz, 2H), 4.03 (d, J=4.9 Hz, 2H), 2.65 (s, 3H), 2.08-1.93 (m, 5H), 1.81-1.66 (m, 1H), 1.37 (s, 3H), 1.29-1.25 (m, 12H). 2 piperidine protons not seen by NMR. LCMS (M+H) calcd for C25H37N4O5: 473.27. found: 473.3.

Provenance & Evidence