N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]prop-2-en-1-amine

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

Procedure: To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3×30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H)+522.3. to afford a yellow slurry to afford a brown solution The aqueous was extracted with ethyl acetate (3×30 cm3) the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3) dried over sodium sulfate, vacuum filtered the volatile fractions removed in vacuo to a crude brown oil The crude product was purified by column chromatography (silica eluting with dichloromethane-methanol 99:1 to 95:5

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

Procedure: To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3×30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H)+522.3. to afford a yellow slurry to afford a brown solution The aqueous was extracted with ethyl acetate (3×30 cm3) the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3) dried over sodium sulfate, vacuum filtered the volatile fractions removed in vacuo to a crude brown oil The crude product was purified by column chromatography (silica eluting with dichloromethane-methanol 99:1 to 95:5

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

Procedure: To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3×30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H)+522.3. to afford a yellow slurry to afford a brown solution The aqueous was extracted with ethyl acetate (3×30 cm3) the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3) dried over sodium sulfate, vacuum filtered the volatile fractions removed in vacuo to a crude brown oil The crude product was purified by column chromatography (silica eluting with dichloromethane-methanol 99:1 to 95:5