4-methylpiperidin-2-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol)in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15. to maintain a temperature less than −69° C Quenched with saturated NaHCO3 extracted with EtOAc Washed the organic layer with brine dried (MgSO4) concentrated in vacuo

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol) in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15. to maintain a temperature less than −69° C Quenched with saturated NaHCO3 extracted with EtOAc Washed the organic layer with brine dried (MgSO4) concentrated in vacuo

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol) in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15. to maintain a temperature less than −69° C Quenched with saturated NaHCO3 extracted with EtOAc Washed the organic layer with brine dried (MgSO4) concentrated in vacuo

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

実験手順: 1.6 g of N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea and 0.2 g of sodium hydroxide are dissolved in 10 ml of water and 50 ml of acetone. With agitation and ice cooling, a solution of 0.85 g of 4-methyl-2-oxo-piperidine-1-carboxylic acid chloride (prepared by reaction of the sodium compound of 4-methyl-2-oxo-piperidine with phosgene) in 20 ml of acetone is added dropwise to this solution, and agitation is continued for 2 hours at room temperature. Subsequently, the acetone is evaporated under reduced pressure, the batch is acidified, suction-filtered, the product is reprecipitated from dilute ammonia and recrystallized from dilute acetone. The N-(4-[2-(4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea obtained has a melting point of 177°-178° C. and is identical with the product obtained according to Example 8. is added dropwise to this solution, and agitation Subsequently, the acetone is evaporated under reduced pressure suction-filtered the product is reprecipitated from dilute ammonia recrystallized from dilute acetone

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol)in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15. to maintain a temperature less than −69° C Quenched with saturated NaHCO3 extracted with EtOAc Washed the organic layer with brine dried (MgSO4) concentrated in vacuo

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol) in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15. to maintain a temperature less than −69° C Quenched with saturated NaHCO3 extracted with EtOAc Washed the organic layer with brine dried (MgSO4) concentrated in vacuo