2,2-dimethyl-3,4-dihydro-1H-quinoline

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

実験手順: A stirred mixture of 2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4.69 g) and 2-bromo-4'-fluoroacetophenone (3.17 g) in dry N,N-dimethylformamide (6 ml) was heated at 70°-80° C. for 5 hours under nitrogen. The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals. The crystals were collected and washed with methanol to give N-(4-fluorobenzoylmethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (3.7 g). was heated at 70°-80° C. for 5 hours under nitrogen The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals The crystals were collected washed with methanol

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

実験手順: This compound was prepared in a manner similar to that described for 1,2,3,4-tetrahydro-2,2-dimethylquinoline (structure 18 of Scheme III, where R1 =R2 =Me) from 2,2-diethyl-1,2-dihydroquinoline (1.46 g, 7.80 mmol) and 10% Pd/C (146 mg, 10% by weight) in EtOAc (18.7 mL) to afford 1.04 g (70%) 2,2-diethyl-1,2,3,4-tetrahydroquinoline after flash chromatography (hexanes:EtOAc, 97:3). Data for 2,2-diethyl-1,2,3,4-tetrahydroquinoline: Rf 0.43 (24:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 6.90-7.00 (m, 2H), 6.57 (td, J=7.3, 1.0, 1H), 6.46 (dd, J=8.4, 1.0, 1H), 3.63 (broad s, 1H), 2.72 (t, J=6.7, 2H), 1.69 (t, J=6.7,2H), 1.38-1.53 (m, 4H), 0.86 (t, J=7.4,6H). This compound was prepared in a manner similar to

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

実験手順: A stirred mixture of 2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4.69 g) and 2-bromo-4'-fluoroacetophenone (3.17 g) in dry N,N-dimethylformamide (6 ml) was heated at 70°-80° C. for 5 hours under nitrogen. The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals. The crystals were collected and washed with methanol to give N-(4-fluorobenzoylmethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (3.7 g). was heated at 70°-80° C. for 5 hours under nitrogen The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals The crystals were collected washed with methanol

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

実験手順: This compound was prepared in a manner similar to that described for 1,2,3,4-tetrahydro-2,2-dimethylquinoline (structure 18 of Scheme III, where R1=R2=Me) from 2,2-diethyl-1,2-dihydroquinoline (1.46 g, 7.80 mmol) and 10% Pd/C (146 mg, 10% by weight) in EtOAc (18.7 mL) to afford 1.04 g (70%) 2,2-diethyl-1,2,3,4-tetrahydroquinoline after flash chromatography (hexanes:EtOAc, 97:3). Data for 2,2-diethyl-1,2,3,4-tetrahydroquinoline: Rf 0.43 (24:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 6.90-7.00 (m, 2H), 6.57 (td, J=7.3, 1.0, 1H), 6.46 (dd, J=8.4, 1.0, 1H), 3.63 (broad s, 1H), 2.72 (t, J=6.7, 2H), 1.69 (t, J=6.7, 2H), 1.38-1.53 (m, 4H), 0.86 (t,J=7.4, 6H). This compound was prepared in a manner similar to

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

実験手順: In a 1 L r.b., a solution of the dihydroquinoline (16.2 g) in 1:1 EtOH:EtOAc (300 mL) was treated with 10% Pd/C (1.05 g) and stirred under an atmosphere of hydrogen. The reaction was monitored by 1H NMR and was complete after 4 h. The reaction mixture was purged, filtered through a pad of Celite, and the pad was rinsed with EtOAc (200 mL). Concentration of the filtrate afforded 16.2 g (99%) of the tetrahydroquinoline as a pale yellow oil. 1H NMR (400 MHz, CDCl3) 6.98 (m, 2H), 6.60 (t, J=7.3, 1H), 6.44 (d, J=8.0, 1H), 2.77 (t, J=6.7, 2H), 1.70 (t, J=6.7, 2H), 1.21 (s, 6H). The reaction mixture was purged filtered through a pad of Celite the pad was rinsed with EtOAc (200 mL)

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

実験手順: This compound was prepared in a manner similar to that described for 1,2,3,4-tetrahydro-2,2-dimethylquinoline (structure 18 of Scheme III, where R1 =R2 =Me) from 2,2-diethyl-1,2-dihydroquinoline (1.46 g, 7.80 mmol) and 10% Pd/C (146 mg, 10% by weight) in EtOAc (18.7 mL) to afford 1.04 g (70%) 2,2-diethyl-1,2,3,4-tetrahydroquinoline after flash chromatography (hexanes:EtOAc, 97:3). Data for 2,2-diethyl-1,2,3,4-tetrahydroquinoline: Rf 0.43 (24:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) 6.90-7.00 (m, 2H), 6.57 (td, J=7.3, 1.0, 1H), 6.46 (dd, J=8.4, 1.0, 1H), 3.63 (broad s, 1H), 2.72 (t, J=6.7, 2H), 1.69 (t, J=6.7,2H), 1.38-1.53 (m, 4H), 0.86 (t, J=7.4,6H). This compound was prepared in a manner similar to

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

実験手順: A stirred mixture of 2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4.69 g) and 2-bromo-4'-fluoroacetophenone (3.17 g) in dry N,N-dimethylformamide (6 ml) was heated at 70°-80° C. for 5 hours under nitrogen. The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals. The crystals were collected and washed with methanol to give N-(4-fluorobenzoylmethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (3.7 g). was heated at 70°-80° C. for 5 hours under nitrogen The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals The crystals were collected washed with methanol