methyl (2S,4S)-4-fluoropyrrolidine-2-carboxylate

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

Procedure: 2.79 g of triethylamine was added under ice cooling and a nitrogen atmosphere to a 50 mL chloroform solution of 1.70 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one and 1.03 g of the compound obtained in step 4-1, after which the reaction mixture was raised to room temperature and stirred for 13 hours at the same temperature. The reaction solution was stirred while a 50 mL saturated sodium hydrogencarbonate aqueous solution was added, and the reaction mixture was stirred for 15 minutes. After liquid separation, the aqueous layer thus obtained was extracted with chloroform. The combined organic layer was washed with saturated brine and dried with magnesium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 2.54 g of residue (yellow, amorphous). The residue thus obtained purified by column chromatography (silica gel 60, mobile phase: ethyl acetate), and stirred and washed in diisopropyl ether to obtain 1.98 g of a diastereoisomer mixture of the titled compound (pale green, amorphous). was added the reaction mixture was stirred for 15 minutes After liquid separation the aqueous layer thus obtained was extracted with chloroform The combined organic layer was washed with saturated brine dried with magnesium sulfate after which the drying agent was filtered off the solvent was distilled off under reduced pressure

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

Procedure: 2.79 g of triethylamine was added under ice cooling and a nitrogen atmosphere to a 50 mL chloroform solution of 1.70 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one and 1.03 g of the compound obtained in step 4-1, after which the reaction mixture was raised to room temperature and stirred for 13 hours at the same temperature. The reaction solution was stirred while a 50 mL saturated sodium hydrogencarbonate aqueous solution was added, and the reaction mixture was stirred for 15 minutes. After liquid separation, the aqueous layer thus obtained was extracted with chloroform. The combined organic layer was washed with saturated brine and dried with magnesium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure to obtain 2.54 g of residue (yellow, amorphous). The residue thus obtained purified by column chromatography (silica gel 60, mobile phase: ethyl acetate), and stirred and washed in diisopropyl ether to obtain 1.98 g of a diastereoisomer mixture of the titled compound (pale green, amorphous). was added the reaction mixture was stirred for 15 minutes After liquid separation the aqueous layer thus obtained was extracted with chloroform The combined organic layer was washed with saturated brine dried with magnesium sulfate after which the drying agent was filtered off the solvent was distilled off under reduced pressure