3-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester → 3-(3-Hydroxy-phenyl)-2-methoxy-propionic acid methyl ester

The compounds of 3-(3-benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester (Example 291, Step 3) (3.15 g, 10.49 mmol) and Pd 10% on activated carbon (0.558 g, 0.524 mmol) were placed in a 250-ml round bottom flask equipped with a magnetic stirring bar. 100 mL of methanol was added, and hydrogen was bubbled through the solution for 10 minutes. The flask was sealed with a rubber septum, and a balloon containing 250 mL of hydrogen was connected to the flask through a needle. The mixture was stirred at room temperature for 5 hours and then concentrated to dryness under vacuum. The residue was taken up in ethyl acetate and filtered through a pad of celite. Concentration of the mixture afforded an oil, 1H-NMR (CDCl3, 200.15 MHz): 7.15 (dt, 1H, J=1.1, 7.0), 6.79–6.68 (m, 3H), 5.27 (br s, 1H), 3.98 (dd, 1H, J=7.5, 5.6), 3.73 (s, 3H), 3.35 (s, 3H), 2.97 (d, 1H, J=3.8), 2.97 (d, 1H, J=9.1).

1. customequipped with a magnetic stirring bar
2. customhydrogen was bubbled through the solution for 10 minutes
3. customThe flask was sealed with a rubber septum
4. additiona balloon containing 250 mL of hydrogen
5. concentrationconcentrated to dryness under vacuum
6. filtrationfiltered through a pad of celite
7. customConcentration of the mixture afforded an oil, 1H-NMR (CDCl3, 200.15 MHz): 7.15 (dt, 1H, J=1.1, 7.0), 6.79–6.68 (m, 3H), 5.27 (br s, 1H), 3.98 (dd, 1H, J=7.5, 5.6), 3.73 (s, 3H), 3.35 (s, 3H), 2.97 (d, 1H, J=3.8), 2.97 (d, 1H, J=9.1)

ORD record

ord-316896fb10cd4e7e99196927c9b0e89e

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192982B2