Pyridine → (R)-2-Hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 1845120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845120
[F:1][C:2]([F:14])([F:13])[C:3]1[N:8]=[CH:7][C:6]([C@@H:9]([OH:12])[CH2:10][OH:11])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:11][CH2:10][C@H:9]([OH:12])[C:6]2[CH:7]=[N:8][C:3]([C:2]([F:13])([F:1])[F:14])=[CH:4][CH:5]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 58188353(R)-1-(6-(Trifluoromethyl)pyridin-3-yl)ethane-1,2-diol

Produkt 1

HCID 86652106(R)-2-Hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of (R)-1-(6-(trifluoromethyl)pyridin-3-yl)ethane-1,2-diol (6.4 g, 31 mmol) and pyridine (20 mL) in CH2Cl2 (200 mL) at 0° C. was added p-toluenesulfonyl chloride (7.0 g, 37 mmol) in small portions. The mixture was slowly warmed to rt and stirred for 40 hours, and then diluted with CH2Cl2 (100 mL). The organic phase was washed with aq. NaHCO3, brine, and dried (Na2SO4), and concentrated to yield the crude title compound.

Aufarbeitung

  1. washThe organic phase was washed with aq. NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5509d6e88b324b4f911c6c1da21dc4cc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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