反应详情

28 mL of DME, 14 mL of tetrahydrofuran and 1.24 mL of acetic acid were added to 2.80 g of methyl 1-piperidin-4-yl-1H-indole-6-carboxylate and 3.16 g of (7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)acetaldehyde. Although crystals precipitated, the reaction mixture was stirred for one hour as it was. The reaction mixture was cooled with an ice-water bath, and 2.75 g of sodium triacetoxyborohydride was added portionwise divided into three to the reaction mixture. The reaction mixture was warmed to room temperature and added with 3 mL of tetrahydrofuran and about 1.5 hours later, progress of the reaction was confirmed. The reaction mixture cooled with an ice-water bath again and added with 68 mL of toluene and 29 mL of water and, after clarification and filtration, added with 30 mL of toluene and the aqueous layer was discarded. The organic layer was washed with 29 mL of 1 N aqueous sodium hydroxide, 29 mL×2 of 5% sodium chloride solution and 29 mL of water. The solvent was evaporated and 5.62 g of the crude title compound was obtained.

1. customAlthough crystals precipitated
2. temperatureThe reaction mixture was cooled with an ice-water bath
3. addition2.75 g of sodium triacetoxyborohydride was added portionwise
4. additionadded with 3 mL of tetrahydrofuran and about 1.5 hours later
5. temperatureThe reaction mixture cooled with an ice-water bath again
6. additionadded with 68 mL of toluene and 29 mL of water
7. filtrationafter clarification and filtration
8. additionadded with 30 mL of toluene
9. washThe organic layer was washed with 29 mL of 1 N aqueous sodium hydroxide, 29 mL×2 of 5% sodium chloride solution and 29 mL of water
10. customThe solvent was evaporated