sodium tetrahydroborate in methanol T=0°C; 0.5 h;

trifluorormethanesulfonic acid in sulfuric acid; 8-Chloro-6-methoxy-11H-benzolt;5,6gt;cycloheptalt;1,2-bgt;pyridin-11-one; 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzolt;5,6gt;cycloheptalt;1,2-bgt;pyridin-5-one

1: 1) NBS, AIBN; 2) DBU / 1) CCl4, reflux, 1.25 h; 2) CH2Cl2, reflux, 1 h 2: 1) AgNO3, Br2; 2) DBU / 1) room temp., 8.5 h; 2) CH2Cl2, reflux, 2.33 h 3: 61 percent / tetrahydrofuran / 1 h / 0 °C 4: 1) 87percent aq. H2SO4; 2) CF3SO3H / 1) room temp., 30 min; 2) 115 deg C, 1 h 5: 84 percent / Et3N / toluene / 0.5 h / 80 °C 6: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 7: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

1: 1) AgNO3, Br2; 2) DBU / 1) room temp., 8.5 h; 2) CH2Cl2, reflux, 2.33 h 2: 61 percent / tetrahydrofuran / 1 h / 0 °C 3: 1) 87percent aq. H2SO4; 2) CF3SO3H / 1) room temp., 30 min; 2) 115 deg C, 1 h 4: 84 percent / Et3N / toluene / 0.5 h / 80 °C 5: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 6: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

1: 61 percent / tetrahydrofuran / 1 h / 0 °C 2: 1) 87percent aq. H2SO4; 2) CF3SO3H / 1) room temp., 30 min; 2) 115 deg C, 1 h 3: 84 percent / Et3N / toluene / 0.5 h / 80 °C 4: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 5: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

1: 84 percent / Et3N / toluene / 0.5 h / 80 °C 2: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 3: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

1: 1) 87percent aq. H2SO4; 2) CF3SO3H / 1) room temp., 30 min; 2) 115 deg C, 1 h 2: 84 percent / Et3N / toluene / 0.5 h / 80 °C 3: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 4: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

1: 67 percent / 13percent aq. KOH / ethanol / 42 h / Heating 2: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme

1: 84 percent / 13percent aq. KOH / ethanol / 24 h / Heating 2: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C View Scheme