Triacetoxyperiodinane → HCID 68843550, compound

Participants

Reaction Steps

[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pyridin-3-yl-methanol (55 mg, 0.112 mmol) was dissolved in methylene chloride. The Dess Martin periodane (0.104 g, 0.224 mmol) was then added to the reaction mixture. The reaction was complete within 10 min and was then diluted with ether. The organic layer was washed with Na2S2O4 (2×30 mL) followed by NaHCO3 (2×30 mL) followed by brine (1×30 mL) The organic layers were combined, dried with Na2SO4 and then evaporated to give [3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pyridin-3-yl-methanone, which was deprotected without further purification. The deprotection was carried out as described for Example 62, except the reaction was complete after 10 min. The product was purified by chromatography to give 17 mg of 3-adamantan-1-yl-4-hydroxy-phenyl)-pyridin-3-yl-methanone as a white solid. 1H NMR (400 MHz, methanol-d4/CDCl3): δ 8.81 (d, J=2.1 Hz, 1H), 8.68 (dd, J=5.0, 1.7 Hz, 1H), 8.07 (td, J=8.0, 2.0 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 7.52 (dd, J=5.0, 2.9 Hz, 1H), 7.48 (dd, J=8.6, 2.5 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 2.10 (d, J=2.9 Hz, 6H), 2.02 (s, 3H), 1.74 (t, J=2.8 Hz, 6H)

Provenance & Evidence