Triacetoxyperiodinane → HCID 54674497, compound

Dess-Martin periodinane (2.181 g, 5.14 mmol) was added to a solution of (3aR,4R,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-ol (1 g, 3.67 mmol) from Example 30 in dichloromethane (24.49 mL). The mixture was stirred for 7 hours and then quenched with 1 N sodium thiosulfate (18 mL) and saturated NaHCO3 solution (12 mL). The mixture was stirred for 1 hour. The organic layer was separated, and concentrated. The crude product was purified by silica gel chromatography using 100% dichloromethane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.51 (t, J=7.9, 1H), 6.99 (d, J=7.3, 1H), 6.48 (d, J=8.6, 1H), 3.84 (dd, J=10.7, 2.8, 1H), 3.65 (dd, J=10.9, 8.6, 1H), 3.52 (dd, J=10.6, 8.7, 1H), 3.17 (dd, J=11.1, 6.3, 1H), 3.00-2.89 (m, 1H), 2.83 (td, J=8.4, 2.9, 1H), 2.39-2.21 (m, 2H), 1.96 (dtd, J=13.4, 8.9, 6.9, 1H), 1.75-1.62 (m, 1H); MS (ESI+) m/z 271 (M+H)+.

1. customquenched with 1 N sodium thiosulfate (18 mL) and saturated NaHCO3 solution (12 mL)
2. stirringThe mixture was stirred for 1 hour
3. customThe organic layer was separated
4. concentrationconcentrated
5. customThe crude product was purified by silica gel chromatography

ORD record

ord-acca7569bc00488fa6118e7519ea7bce

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796470B2