Tetrabutylammonium Fluoride → 7-[2-(4-Biphenyl-3-yl-3-hydroxy-butyl)-5-oxo-pyrrolidin-1-yl]-heptanenitrile

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Reaction Steps

Following the procedure described for Example 5, Step B, 7-{2-[4-biphenyl-3-yl-3-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (187 mg, 0.351 mmol) was deprotected with TBAF (1M in THF, 0.53 mL, 0.53 mmol). The addition was performed at 0° C. and the reaction mixture was stirred at room temperature for 24 h. Purification by medium pressure chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% MeOH in CH2Cl2 to 6% MeOH in CH2Cl2 to 10% MeOH in CH2Cl2) provided 7-[2-(4-biphenyl-3-yl-3-hydroxy-butyl)-5-oxo-pyrrolidin-1-yl]-heptanenitrile (85 mg). 1H NMR (CDCl3) δ7.58 (m, 1H), 7.51-7.33 (m, 4H), 7.21-7.12 (m, 4H), 3.85 (m, 1H), 3.60 (m, 2H), 2.90 (m, 1H), 2.83-2.60 (m, 2H), 2.45-2.30 (m, 4H), 2.14 (m, 1H), 1.73-1.25 (m, 14H).

Provenance & Evidence