Tetrabutylammonium Fluoride → (2S,4R)-methyl 4-(4'-(dimethylamino)-2'-vinylbiphenyl-4-yl)-4-methoxypyrrolidine-2-carboxylate

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Reaction Steps

TBAF (1.0M in THF, 1.7 mL, 1.7 mmol) was added to a solution of (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-(4′-(dimethylamino)-2′-vinylbiphenyl-4-yl)-4-methoxypyrrolidine-1,2-dicarboxylate (231 mg, 0.440 mmol) in THF (5 mL) and stirred at r.t. for 1 hr. The reaction was evaporated to give crude (2S,4R)-methyl 4-(4′-(dimethylamino)-2′-vinylbiphenyl-4-yl)-4-methoxypyrrolidine-2-carboxylate (167 mg, 0.439 mmol, 100% yield) as an orange oil used directly in next steps with no purification. LCMS: rt=1.01 min. [M-OMe]+=349; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 μL; wavelength=220.

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