Triethylamine → 3-(4-Hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid methyl ester

Trifluoroacetic anhydride (0.62 mL, 4.36 mmol) and triethylamine (0.62 mL, 4.36 mmol) were added to a solution of 3-(4-benzyloxy-3-methoxy-phenyl)-3-hydroxy-2-methoxy-propionic acid methyl ester (1.01 g, 2.91 mmol) in methylene chloride (30 mL) at 0° C. The resulting mixture was stirred for 4 hours at room temperature and was concentrated under vacuum. The residue was dissolved in ethyl acetate (30 mL), and 10% palladium on carbon (0.3 g) was added to the solution. The mixture was stirred under hydrogen pressure (4 atm) for 16 hours. The mixture was filtered through Celite and concentrated under vacuum. The residue was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate 7:3) to produce 3-(4-hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid methyl ester as an oil (598 mg, 86%). 1H-NMR (200.15 MHz, CDCl3): δ 6.80 (d, 1H, J=7.8), 6.7 (s, 1H), 6.62 (d, 1H, J=7.8), 3.96 (dd, 1H, J=7.8, 4.0), 3.80 (s, 3H), 3.68 (s, 3H), 3.30 (s, 3H), 3.09 (dd, 1H, J=14.2, 4.0), 2.91 (dd, 1H, J=14.2, 7.8).

1. concentrationwas concentrated under vacuum
2. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
3. addition10% palladium on carbon (0.3 g) was added to the solution
4. stirringThe mixture was stirred under hydrogen pressure (4 atm) for 16 hours
5. filtrationThe mixture was filtered through Celite
6. concentrationconcentrated under vacuum
7. customThe residue was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate 7:3)

ORD record

ord-78a76c8d5c954372aba6aed127820609

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192982B2