Sodium bis(acetyloxy)boranuidyl acetate → Isopropyl 2-(3-((7-(3-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)phenoxy)acetate

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Reaction Steps

To a solution of isopropyl 2-(3-((7-(3-fluorophenyl)-3,4-dihydronaphthalen-1(2H)-ylidene)amino)phenoxy)acetate (25 mg, 0.057 mmol) and methanol (2 mL) was added sodium triacetoxyborohyride (12 mg, 0.057 mmol) at 0° C. The solution was stirred for 4 hours at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 9 mg (36%) of isopropyl 2-(3-((7-(3-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)phenoxy)acetate.

Provenance & Evidence