11,12-dihydro-5H-benzo[c][1]benzazocin-6-one

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

実験手順: To a suspension of 11,12-dihydro-5H-dibenzo[b,f]azocin-6-one (2.0 g, 8.96 mmol) in dry THF (20 ml) is added dropwise a solution of LiAlH4 (1.0 N in THF, 8.96 ml) over a period of 10 min. After ceasing of gas evolution, the reaction mixture is kept stirring at reflux overnight, then quenched by the addition of water (0.48 ml). The precipitate is filtered off and the filtrate is extracted twice with EtOAc. The combined organic layers are dried over Na2SO4, the solvent is evaporated and the residue recrystallized from boiling hexane to give off white crystals of the title compound (1.35 g) in 72% yield: tR (LC-2) 1.65 min; ESI-MS(+): m/z 210.70 [M+H]+ (calcd 209.29 for C15H15N). at reflux overnight quenched by the addition of water (0.48 ml) The precipitate is filtered off the filtrate is extracted twice with EtOAc The combined organic layers are dried over Na2SO4 the solvent is evaporated the residue recrystallized

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

実験手順: To a suspension of 11,12-dihydro-5H-dibenzo[b,f]azocin-6-one (2.0 g, 8.96 mmol) in dry THF (20 ml) is added dropwise a solution of LiAlH4 (1.0 N in THF, 8.96 ml) over a period of 10 min. After ceasing of gas evolution, the reaction mixture is kept stirring at reflux overnight, then quenched by the addition of water (0.48 ml). The precipitate is filtered off and the filtrate is extracted twice with EtOAc. The combined organic layers are dried over Na2SO4, the solvent is evaporated and the residue recrystallized from boiling hexane to give off white crystals of the title compound (1.35 g) in 72% yield: tR (LC-2) 1.65 min; ESI-MS(+): m/z 210.70 [M+H]+ (calcd 209.29 for C15H15N). at reflux overnight quenched by the addition of water (0.48 ml) The precipitate is filtered off the filtrate is extracted twice with EtOAc The combined organic layers are dried over Na2SO4 the solvent is evaporated the residue recrystallized

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

実験手順: In a two liter three neck round bottom flask (argon atmosphere) was placed 300 ml of dry THF and 30.06 g (0.8 mole) of LAH was added cautiously. The reaction mixture was stirred and a suspension of 89.31 g (0.4 mole) of 11,12-dihydrodibenz[b,f]azocin-6(5H)-one (Aldrich) in 400 ml of hot THF was added dropwise. After the addition, the reaction mixture was stirred and heated to reflux for 8.5 hr. The reaction mixture was cooled to RT and 60 ml of 1N sodium hydroxide was added with caution (hydrogen evolution). The reaction mixture was stirred and heated to reflux for 0.5 hr to give a white suspension. The solid was removed by filtration and washed with several portions of warm THF. The filtrate was concentrated to dryness in vacuo to give 82.5 g of white solid title compound of 99.5% purity by g.c. The product was used in the next step without further purification. was added cautiously was added dropwise After the addition the reaction mixture was stirred heated to reflux for 8.5 hr The reaction mixture was stirred heated to reflux for 0.5 hr to give a white suspension The solid was removed by filtration washed with several portions of warm THF The filtrate was concentrated to dryness in vacuo

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

実験手順: In a two liter three neck round bottom flask (argon atmosphere) was placed 300 ml of dry THF and 30.06 g (0.8 mole) of LAH was added cautiously. The reaction mixture was stirred and a suspension of 89.31 g (0.4 mole) of 11,12-dihydrodibenz[b,f]azocin-6(5H)-one (Aldrich) in 400 ml of hot THF was added dropwise. After the addition, the reaction mixture was stirred and heated to reflux for 8.5 hr. The reaction mixture was cooled to RT and 60 ml of 1N sodium hydroxide was added with caution (hydrogen evolution). The reaction mixture was stirred and heated to reflux for 0.5 hr to give a white suspension. The solid was removed by filtration and washed with several portions of warm THF. The filtrate was concentrated to dryness in vacuo to give 82.5 g of white solid title compound of 99.5% purity by g.c. The product was used in the next step without further purification. was added cautiously was added dropwise After the addition the reaction mixture was stirred heated to reflux for 8.5 hr The reaction mixture was stirred heated to reflux for 0.5 hr to give a white suspension The solid was removed by filtration washed with several portions of warm THF The filtrate was concentrated to dryness 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 11,12-dihydro-5H-dibenzo[b,f]azocin-6-one (2.0 g, 8.96 mmol) in dry THF (20 ml) is added dropwise a solution of LiAlH4 (1.0 N in THF, 8.96 ml) over a period of 10 min. After ceasing of gas evolution, the reaction mixture is kept stirring at reflux overnight, then quenched by the addition of water (0.48 ml). The precipitate is filtered off and the filtrate is extracted twice with EtOAc. The combined organic layers are dried over Na2SO4, the solvent is evaporated and the residue recrystallized from boiling hexane to give off white crystals of the title compound (1.35 g) in 72% yield: tR (LC-2) 1.65 min; ESI-MS(+): m/z 210.70 [M+H]+ (calcd 209.29 for C15H15N). at reflux overnight quenched by the addition of water (0.48 ml) The precipitate is filtered off the filtrate is extracted twice with EtOAc The combined organic layers are dried over Na2SO4 the solvent is evaporated the residue recrystallized

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

実験手順: In a two liter three neck round bottom flask (argon atmosphere) was placed 300 ml of dry THF and 30.06 g (0.8 mole) of LAH was added cautiously. The reaction mixture was stirred and a suspension of 89.31 g (0.4 mole) of 11,12-dihydrodibenz[b,f]azocin-6(5H)-one (Aldrich) in 400 ml of hot THF was added dropwise. After the addition, the reaction mixture was stirred and heated to reflux for 8.5 hr. The reaction mixture was cooled to RT and 60 ml of 1N sodium hydroxide was added with caution (hydrogen evolution). The reaction mixture was stirred and heated to reflux for 0.5 hr to give a white suspension. The solid was removed by filtration and washed with several portions of warm THF. The filtrate was concentrated to dryness in vacuo to give 82.5 g of white solid title compound of 99.5% purity by g.c. The product was used in the next step without further purification. was added cautiously was added dropwise After the addition the reaction mixture was stirred heated to reflux for 8.5 hr The reaction mixture was stirred heated to reflux for 0.5 hr to give a white suspension The solid was removed by filtration washed with several portions of warm THF The filtrate was concentrated to dryness in vacuo