4-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime → [5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]methanol

Participants

Reaction Steps

A solution of Clorox® was added dropwise (1 mL) to a solution of the product from step 24a (0.52 g, 2.56 mmol) and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime (0.5 g, 1.71 mmol) from step 1b in THF (4 mL) under nitrogen atmosphere at room temperature. The reaction was stirred overnight, partitioned between ethyl acetate and water saturated with KH2PO4. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting methylene chloride:ethyl acetate (50:50) to give {5-(tert-butyl-dimethyl-silanyloxymethyl)-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-methanol (0.51 g, 61%) as an oil. MS found: (M+H)+=493.

Provenance & Evidence