Tetrabutylammonium Fluoride → (2S,4R)-methyl 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylate

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Reaction Steps

TBAF (1.0M in THF, 19 mL, 19 mmol) was added to a solution of (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-methoxy-4-(3′-vinylbiphenyl-3-yl)pyrrolidine-1,2-dicarboxylate (2.3 g, 4.78 mmol) in THF (30 mL) and stirred at r.t. overnight. The reaction was diluted with EtOAc and washed with water and then brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give (2S,4R)-methyl 4-methoxy-4-(3′-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylate (1.75 g, 5.19 mmol, 100% yield) as a yellow oil. LCMS: rt=1.42 min. [M-OMe]+=306; 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 uL; wavelength=220.

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