Dimethylformamide → Hydratropamide, alpha-methyl-

Temperature

23 °C

To a solution of 2-methyl-2-phenylpropionic acid in 100 mL of CH2Cl2 was added 0.50 mL of DMF and oxalyl chloride (3.40 g, 26.8 mmol). The mixture was stirred at 23° C. for 4 hours then the solvent was removed under reduced pressure. The crude material was dissolved in 50 mL of THF and 30 mL of NH4OH was added. The mixture was stirred at 23° C. for 1 hour then and the mixture was concentrated under reduced pressure. The crude product was dissolved in 150 mL of EtOAc and washed with 100 mL of 2 N HCl, 100 mL NaHCO3, and 100 mL of brine. The organic phase was dried over Na2SO4 and concentrated. The product was purified by recrystallization from EtOAc/hexanes to provide 3.50 g (88% yield) of the desired product as a white powder.

1. customthe solvent was removed under reduced pressure
2. dissolutionThe crude material was dissolved in 50 mL of THF
3. addition30 mL of NH4OH was added
4. stirringThe mixture was stirred at 23° C. for 1 hour
5. concentrationthe mixture was concentrated under reduced pressure
6. dissolutionThe crude product was dissolved in 150 mL of EtOAc
7. washwashed with 100 mL of 2 N HCl, 100 mL NaHCO3, and 100 mL of brine
8. dry with materialThe organic phase was dried over Na2SO4
9. concentrationconcentrated
10. customThe product was purified by recrystallization from EtOAc/hexanes

ORD record

ord-e252db8fb7e14dabbd4c0db62e75b4eb

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06495576B2