tert-Butyl methyl ether → HCID 86670385, Verbindung

Temperatur

100 °C

A 15-mL reaction vial was charged with 4-(phenylsulfonyl)piperidine (1.05 g, 4.66 mmol, BetaPharma, Brandford, Conn.), sodium t-butoxide (0.98 g, 10.24 mmol), 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (1.50 g, 4.66 mmol, Bioorg. Med. Chem. Lett. 2002, 12, 3009), chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (RuPhos Palladacycle) (0.170 g, 0.233 mmol, Strem Chemicals, Inc, Newburyport, Mass.), and toluene (10 mL). The vial was closed and purged with nitrogen for several minutes. The reaction mixture was heated at 100° C. for 2.5 h and allowed to cool to room temperature. The reaction mixture was diluted with water (5 mL) and extracted with EtOAc (10 mL). The organic extract was washed with water (5 mL) and dried over Na2SO4. The solution was filtered and concentrated and then absorbed onto a plug of silica gel and purified by column chromatography (40 g of silica gel, 10 to 30% EtOAc in hexanes) to provide 1,1,1,3,3,3-hexafluoro-2-(4-(4-(phenylsulfonyl)piperidin-1-yl)phenyl)-2-propanol (1.94 g) as white solid

1. customA 15-mL reaction
2. customThe vial was closed
3. custompurged with nitrogen for several minutes
4. temperatureto cool to room temperature
5. additionThe reaction mixture was diluted with water (5 mL)
6. extractionextracted with EtOAc (10 mL)
7. extractionThe organic extract
8. washwas washed with water (5 mL)
9. dry with materialdried over Na2SO4
10. filtrationThe solution was filtered
11. concentrationconcentrated
12. customabsorbed onto a plug of silica gel
13. custompurified by column chromatography (40 g of silica gel, 10 to 30% EtOAc in hexanes)

ORD-Eintrag

ord-f30c314bfadb4c6d80ea8fae71208128

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08431563B2