3,3-dibromoazepan-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:; See reaction.notes.procedure_details.

実験手順: A solution of 16 g (59 mmol) of 3,3-dibromoazacycloheptan-2-one, 150 ml of glacial acetic acid, 5.5 g (65 mmol) of sodium acetate, and 0.5 g of palladium on carbon (10%) was placed in a hydrogenator bottle and reduced under hydrogen at 30 psi. The mixture was filtered, and the filtrate distilled under vacuum to remove the acetic acid. The residue was neutralized with sat. Na2CO3, extracted into CH2Cl2, dried over MgSO4, and concentrated to yield 10.8 g (95%) of the product as an off-white solid; mp 109°-111° C.; NMR (CDCl3) 7.2 (1 H,m), 4.6 (1 H,m), 3.4 (2 H,m), 2.1 (4 H,m), 1.7 (2 H,m). The mixture was filtered the filtrate distilled under vacuum to remove the acetic acid extracted into CH2Cl2 dried over MgSO4 concentrated

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

実験手順: To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one. the reaction at room temperature for several hours quench with aqueous NaHSO3 isolate the organic phase dry concentrate in vacuo

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

実験手順: To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one. the reaction at room temperature for several hours quench with aqueous NaHSO3 isolate the organic phase dry concentrate in vacuo

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

実験手順: A solution of 16 g (59 mmol) of 3,3-dibromoazacycloheptan-2-one, 150 ml of glacial acetic acid, 5.5 g (65 mmol) of sodium acetate, and 0.5 g of palladium on carbon (10%) was placed in a hydrogenator bottle and reduced under hydrogen at 30 psi. The mixture was filtered, and the filtrate distilled under vacuum to remove the acetic acid. The residue was neutralized with sat. Na2CO3, extracted into CH2Cl2, dried over MgSO4, and concentrated to yield 10.8 g (95%) of the product as an off-white solid; mp 109°-111° C.; NMR (CDCl3) 7.2 (1 H,m), 4.6 (1 H,m), 3.4 (2 H,m), 2.1 (4 H,m), 1.7 (2 H,m). The mixture was filtered the filtrate distilled under vacuum to remove the acetic acid extracted into CH2Cl2 dried over MgSO4 concentrated

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

実験手順: To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one. the reaction at room temperature for several hours quench with aqueous NaHSO3 isolate the organic phase dry concentrate in vacuo

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

実験手順: To a suspension of 300 mg of sodium hydride in 25 ml THF add a solution of 2.71 g of 3,3-dibromoperhydroazepin-2-one [R. Wineman et al., J. Am. Chem. Soc., 80, 6233 (1958)] and 2.50 g of t-butyl iodoacetate in 25 ml THF, carrying out the operation under N2. Stir the reaction at room temperature for several hours, quench with aqueous NaHSO3, isolate the organic phase, dry and concentrate in vacuo to obtain 1-t-butoxycarbonylmethyl-3,3-dibromoperhydroazepin-2-one. the reaction at room temperature for several hours quench with aqueous NaHSO3 isolate the organic phase dry concentrate in vacuo