Tetrahydrofuran → 1-(2-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-yl)ethane-1,2-diol

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Reaction Steps

To 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)isoxazole (Preparation 82E, 0.2 g, 0.471 mmol) in THF (3 mL) were sequentially added osmium tetroxide (4% aq.) (0.148 mL, 0.019 mmol) and NMO (50% aq.) (0.22 mL, 0.471 mmol) at room temperature and the contents were stirred overnight under a nitrogen atmosphere. The same reaction was setup in a different flask. The reaction mixtures from both flasks were combined and concentrated. The residue was partitioned between dichloromethane (40 mL) and water (10 mL). The dichloromethane layer was separated, dried over sodium sulfate and concentrated. To the solid was added acetonitrile (10 mL), the contents were triturated, sonicated and filtered. The solid was washed with acetonitrile (2×3 mL) and dried to yield 240 mgs of a pale yellow solid. The filtrate was concentrated and purified by silica gel column chromatography using an ISCO setup. (24 g, RediSep® silica gel column). The desired fractions were collected and concentrated to yield another 55 mgs of a pale yellow solid. The compound had an HPLC retention time=3.69 min. (condition C); LC/MS M+1=459; 1H NMR (400 MHz, CDCl3) δ ppm 7.66 (2H, d, J=6.6 Hz), 7.48-7.58 (3H, m), 7.41 (1H, d, J=7.7 Hz), 7.28-7.36 (2H, m), 4.82-4.90 (1H, m), 3.83 (1H, ddd, J=11.0, 7.3, 3.5 Hz), 3.71 (1H, td, J=7.5, 4.0 Hz), 3.13-3.25 (4H, m), 2.63 (1H, OH, d, J=3.3 Hz).

Provenance & Evidence