反应详情

Dimethylamide 22.1 (2.1 g, 4.23 mmol) was dissolved in 50 mL of EtOAc, and nitrogen was bubbled through the solution for 5 minutes. 1 g of palladium on carbon (5 wt. %, wet contains 50% water) was added, and a hydrogen balloon was attached. After 8 hours, the mixture was filtered through a plug of silica with 10% MeOH in EtOAc. The organic layer was concentrated under reduced pressure and partitioned between ACN (100 mL) and hexane (50 mL). The ACN layer was washed with hexane (4×50 mL). The ACN layer was concentrated under reduced pressure to afford (S)-methyl 4-(dimethylamino)-3-(4-hydroxyphenyl)-4-oxobutanoate 22.2 (1.0 g, 3.98 mmol) as a colorless oil. MS ESI (pos.) m/e: 252.4 (M+H)+.

1. customnitrogen was bubbled through the solution for 5 minutes
2. addition1 g of palladium on carbon (5 wt. %, wet contains 50% water) was added
3. filtrationthe mixture was filtered through a plug of silica with 10% MeOH in EtOAc
4. concentrationThe organic layer was concentrated under reduced pressure
5. custompartitioned between ACN (100 mL) and hexane (50 mL)
6. washThe ACN layer was washed with hexane (4×50 mL)
7. concentrationThe ACN layer was concentrated under reduced pressure