ethyl 6-oxopiperidine-3-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4° C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: MS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1H NMR (CDCl3) δ1.42-1.60 (m, 1H), 1.60-2.05 (m, 2H), 2.10-2.47 (m, 2H), 3.05 (t, J=9 Hz, 1H), 3.21-3.58 (m, 4H), 6.85 (s, 1H). The mixture was filtered the granular precipitate washed with 100 ml THF Evaporation of the combined filtrate and washings

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H). The resulting solution was evaporated to dryness the residue triturated with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4° C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: NS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1H NMR (CDCl3) δ1.42-1.60 (m, 1H), 1.60-2.05 (m, 2H), 2.10-2.47 (m, 2H), 3.05 (t, J=9 Hz, 1H), 3.21-3.58 (m, 4H), 6.85 (s, 1H). The mixture was filtered the granular precipitate washed with 100 ml THF Evaporation of the combined filtrate and washings

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H). The resulting solution was evaporated to dryness the residue triturated with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H). The resulting solution was evaporated to dryness the residue triturated with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4° C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: MS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1H NMR (CDCl3) δ1.42-1.60 (m, 1 H), 1.60-2.05 (m, 2 H), 2.10-2.47 (m, 2 H), 3.05 (t, J=9 Hz, 1 H), 3.21-3.58 (m, 4 H), 6.85 (s, 1 H). The mixture was filtered the granular precipitate washed with 100 ml THF Evaporation of the combined filtrate and washings

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3 H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1 H), 2.15-2.31 (m, 2 H), 2.78-2.89 (m, 1 H), 3.25-3.40 (m, 2 H), 4.12 (t, J=7 Hz, 2 H), 7.95 (s, 1 H). The resulting solution was evaporated to dryness the residue triturated with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3 H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1 H), 2.15-2.31 (m, 2 H), 2.78-2.89 (m, 1 H), 3.25-3.40 (m, 2 H), 4.12 (t, J=7 Hz, 2 H), 7.95 (s, 1 H). The resulting solution was evaporated to dryness the residue triturated with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4° C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: MS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1H NMR (CDCl3) δ1.42-1.60 (m, 1H), 1.60-2.05 (m, 2H), 2.10-2.47 (m, 2H), 3.05 (t, J=9 Hz, 1H), 3.21-3.58 (m, 4H), 6.85 (s, 1H). The mixture was filtered the granular precipitate washed with 100 ml THF Evaporation of the combined filtrate and washings

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H). The resulting solution was evaporated to dryness the residue triturated with ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4° C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: NS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1H NMR (CDCl3) δ1.42-1.60 (m, 1H), 1.60-2.05 (m, 2H), 2.10-2.47 (m, 2H), 3.05 (t, J=9 Hz, 1H), 3.21-3.58 (m, 4H), 6.85 (s, 1H). The mixture was filtered the granular precipitate washed with 100 ml THF Evaporation of the combined filtrate and washings

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 250 g of 5-carboxy-2-piperidone in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22° C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1H NMR (DMSO-d6) δ1.21 (t, J=7 Hz, 3H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1H), 2.15-2.31 (m, 2H), 2.78-2.89 (m, 1H), 3.25-3.40 (m, 2H), 4.12 (t, J=7 Hz, 2H), 7.95 (s, 1H). The resulting solution was evaporated to dryness the residue triturated with ether