Ammonium Chloride → (S)-2-tert-Butoxycarbonylamino-5-oxo-non-8-enoic acid benzyl ester

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To a solution of (S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (Org. Lett. 2004, 5, 1469; 450 mg, 1.41 mmol) in THF (10 mL) was added 3-butenylmagnesium bromide solution (0.5 M in THF, 3.38 mL, 1.69 mmoL) at −40° C., then after 3 h sat. aq. ammonium chloride solution (5 mL) was added. The reaction mixture was partitioned between EtOAc and water, the organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 2:1) afforded the title compound (329 mg, 62%). Colourless oil, MS: 376.4 (M+H)+.

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