Trifluoroacetic acid → HCID 57482557, compound

3-methoxy-2-methoxymethoxy-5-(2-oxopyrrolidin-1-yl)benzaldehyde (0.72 g, 2.56 mmol) was dissolved in a solvent mixture of acetic acid (5 ml) and ethanol (7 ml) and 10% palladium carbon (70 mg) was added thereto to perform catalytic reduction at 50° C. for 10 hours. The reaction solution was cooled to room temperature and filtrated by cerite. The filtered cake was concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane (15 ml) and trifluoroacetic acid (2.0 ml, 25.6 mmol) and triethylsilane (2.0 ml, 12.8 mmol) were added thereto under ice cooling. The mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→ethyl acetate). The purified product was concentrated under reduced pressure to obtain 1-(4-hydroxy-3-methoxy-5-methylphenyl)pyrrolidin-2-one (0.41 g) as light yellow oil.

1. additionwas added
2. customat 50° C.
3. customfor 10 hours
4. filtrationfiltrated by cerite
5. concentrationThe filtered cake was concentrated under reduced pressure
6. customThe residue thus obtained
7. concentrationThe mixture was concentrated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→ethyl acetate)
9. concentrationThe purified product was concentrated under reduced pressure

ORD record

ord-f6b8fa98a23d49ffaaf43d8f77eaa0e1

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071600B2