反应详情

To a solution of 3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzaldehyde (Example 50, step A, 6.1 g) and 2-(2-aminoethyl)pyridine (3.18 g, 3.1 ml) in toluene (150 mL) was added p-toluene sulfonic acid (100 mg). The reaction was heated at reflux in a Dean-Stark apparatus for couple of hours. Around 2 mL water were displaced. The mixture was cooled and washed with aqueous bicarbonate and concentrated in vacuo. The residue was taken up in ethanol (100 ml) and cooled. Sodium borohydride (1.0 g) was added slowly and the reaction left 1 hour to warm to room temperature. Water was added (100 mL) and ethanol removed by distillation. The reaction was partitioned between aqueous bicarbonate and ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to give yellow oil (6.5 g). The material was used in the next step without further purification.

1. temperatureThe reaction was heated
2. temperatureat reflux in a Dean-Stark apparatus for couple of hours
3. temperatureThe mixture was cooled
4. washwashed with aqueous bicarbonate
5. concentrationconcentrated in vacuo
6. temperaturecooled
7. additionSodium borohydride (1.0 g) was added slowly
8. additionWater was added (100 mL) and ethanol
9. customremoved by distillation
10. customThe reaction was partitioned between aqueous bicarbonate and ethyl acetate
11. dry with materialThe organic layers were dried over sodium sulfate
12. concentrationconcentrated in vacuo