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With sodium hydroxide In tetrahydrofuran; 1,4-dioxane |
41.2 8-Methoxy-2,3,4,5-tetrahydro-1H-benz[c]azepine
Step 2 8-Methoxy-2,3,4,5-tetrahydro-1H-benz[c]azepine To a solution of lithium aluminum hydride (3.07 g) in tetrahydrofuran (60 ml) was dropwise added a solution of 8-methoxy-2,3,4,5-tetrahydrobenz[c]azepin-1-one (4.42 g) in 1,4-dioxane (30 ml) with ice-cooling and the mixture was refluxed for 20 hours. After completion of the reaction, 20% aqueous sodium hydroxide solution was added dropwise with ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was filtrated, and the solvent was evaporated and the residue was dried under reduced pressure to give the title compound (4.05 g). 1H-NMR (δ ppm, CDCl3) 1.68 (m, 2H), 2.82-2.90 (m, 2H), 3.10-3.25 (m, 2H), 3.77 (s, 3H), 3.88 (s, 2H), 6.60-6.70 (2H), 7.05 (1H). |
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With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 80℃; for 1.5h; Heating / reflux; |
81.2
8-methoxy-2,3,4,5-tetrahydro-benzo[C]-azepin-l-one (0.512 g, 2.68 mmol) was stirred in anhydrous tetrahydrofiiran (13.4 mL) at room temperature under nitrogen. A solution of lithium aluminum hydride in tetrahydrofiiran (IM, 4.02 mL) was added dropwise via syringe to the clear solution. The resulting reaction mixture was refluxed at 8O0C for 1.5 hours. The reaction was cooled to room temperature and then brought to O0C with an ice bath. This was quenched by slow addition of saturated potassium sodium tartrate. The biphase was stirred at room temperature for 30 minutes and extracted with ethyl acetate (2x). The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as a clear oil. |