Methanol → HCID 57522146, Verbindung

To a solution (92 mL) of 5-phenyl-1H-pyrrole-3-carbaldehyde (0.92 g) in methanol was added 40% methylamine solution (1.26 g) at room temperature and the mixture was stirred for 30 min. To the reaction mixture was added sodium borohydride (305 mg) at room temperature and the mixture was stirred for 10 min. Water (200 mL) was added and the mixture was further stirred for 1 hr. Saturated brine (50 mL) was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetonitrile (48 mL), and di-tert-butyl bicarbonate (1.41 g) was added dropwise at room temperature. The mixture was stirred for 1.5 hr and partitioned with water and ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as colorless crystals (yield 0.99 g, 64%).

1. stirringthe mixture was stirred for 10 min
2. stirringthe mixture was further stirred for 1 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in acetonitrile (48 mL)
8. additiondi-tert-butyl bicarbonate (1.41 g) was added dropwise at room temperature
9. stirringThe mixture was stirred for 1.5 hr
10. custompartitioned with water and ethyl acetate
11. washThe ethyl acetate layer was washed with saturated brine
12. dry with materialdried over anhydrous sodium sulfate
13. concentrationconcentrated under reduced pressure
14. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

ORD-Eintrag

ord-ac3ca403bcfe44e396a957ac40052656

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08048909B2