(2S)-2-phenyl-2-(prop-2-enylamino)-1-pyrrolidin-1-ylethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of N-allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (66.2 g, 154 mmol) in anhydrous dimethylformamide (300 cm3) was added potassium carbonate (63.9 g, 462 mmol). The mixture was stirred at ambient temperature for 10 minutes and thiophenol (22.2 cm3, 216 mmol) was added dropwise over 10 minutes. The mixture was stirred for 16 hours at ambient temperature and poured into water (2000 cm3) and extracted with ethyl acetate (3×500 cm3). The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a foul smelling yellow oil. The crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1 and then dichloromethane-methanol 19:1 to 9:1) to afford the title compound as a yellow viscous oil (31.9 g, 84.9%) with a positive ion ESI (M+H)+245.3. The mixture was stirred for 16 hours at ambient temperature extracted with ethyl acetate (3×500 cm3) The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3) dried over sodium sulfate, vacuum filtered the volatile fractions removed in vacuo to a foul smelling yellow oil The crude product was purified by column chromatography (silica eluting with hexane-ethyl acetate 1:1 to 0:1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of N-allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (66.2 g, 154 mmol) in anhydrous dimethylformamide (300 cm3) was added potassium carbonate (63.9 g, 462 mmol). The mixture was stirred at ambient temperature for 10 minutes and thiophenol (22.2 cm3, 216 mmol) was added dropwise over 10 minutes. The mixture was stirred for 16 hours at ambient temperature and poured into water (2000 cm3) and extracted with ethyl acetate (3×500 cm3). The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a foul smelling yellow oil. The crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1 and then dichloromethane-methanol 19:1 to 9:1) to afford the title compound as a yellow viscous oil (31.9 g, 84.9%) with a positive ion ESI (M+H)+245.3. The mixture was stirred for 16 hours at ambient temperature extracted with ethyl acetate (3×500 cm3) The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3) dried over sodium sulfate, vacuum filtered the volatile fractions removed in vacuo to a foul smelling yellow oil The crude product was purified by column chromatography (silica eluting with hexane-ethyl acetate 1:1 to 0:1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of N-allyl-2-nitro-N-(2-oxo-1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (66.2 g, 154 mmol) in anhydrous dimethylformamide (300 cm3) was added potassium carbonate (63.9 g, 462 mmol). The mixture was stirred at ambient temperature for 10 minutes and thiophenol (22.2 cm3, 216 mmol) was added dropwise over 10 minutes. The mixture was stirred for 16 hours at ambient temperature and poured into water (2000 cm3) and extracted with ethyl acetate (3×500 cm3). The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a foul smelling yellow oil. The crude product was purified by column chromatography (silica, eluting with hexane-ethyl acetate 1:1 to 0:1 and then dichloromethane-methanol 19:1 to 9:1) to afford the title compound as a yellow viscous oil (31.9 g, 84.9%) with a positive ion ESI (M+H)+245.3. The mixture was stirred for 16 hours at ambient temperature extracted with ethyl acetate (3×500 cm3) The combined ethyl acetate extracts were washed with water (2×400 cm3), brine (1×300 cm3) dried over sodium sulfate, vacuum filtered the volatile fractions removed in vacuo to a foul smelling yellow oil The crude product was purified by column chromatography (silica eluting with hexane-ethyl acetate 1:1 to 0:1