Imidazole → N-Allyl-N-{2-[3-(S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-1-yl]-2-oxo-1-(S)-phenyl-ethyl}-2-nitro-benzenesulfonamide

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To a stirred solution N-allyl-N-[2-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-oxo-1-(S)-phenyl-ethyl]-2-nitro-benzenesulfonamide (7.13 g, 16.0 mmol) in anhydrous dimethylformamide (16 cm3) was added imidazole (2.18 g, 32.0 mmol). When the imidazole dissolved tert-butyldimethylsilyl chloride was added and stirred at ambient temperature for 3 hours. The solution was poured into water (200 cm3), extracted with ethyl ether (3×50 cm3), washed with water (2×40 cm3), brine (40 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a yellow glass (8.73 g, 97.4%) with a positive ion ESI (M+H)+560.3

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