Potassium Carbonate → 3-Hydroxybutyl 4-methylbenzenesulfonate

HRID 55657

Reaktionsgleichung

Reaktionsgleichung von HRID 55657
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].F[C:13]1C=C[C:16]2C(C3CCNCC3)=N[O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O:4][CH2:13][CH2:14][CH:15]([OH:19])[CH3:16])(=[O:3])=[O:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 85570p-ToluenesulfonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Produkt 1

HCID 132043233-Hydroxybutyl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Racemic 3-hydroxybutyl tosylate was prepared in a manner described by Ferreira et al., Tetrahedron, 46, pp. 6311-6318, (1990). To a solution of the racemic tosylate (9.2 g, 37.7 mmol) in acetonitrile (190 ml) was added 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (8.3 g, 37.7 mmol) followed by milled potassium carbonate (7.8 g, 56.6 mmol) at room temperature under nitrogen. The reaction mixture was warmed to reflux for 4.5 hours and allowed to cool to room temperature. The solids were removed via filtration through a pad of Celite and were washed with EtOAc. The combined filtrates were concentrated to give the crude product. Purification via preparative HPLC (silica gel, 10% MeOH/EtOAc) afforded 6.3 g (57%), m.p.=100°-102° C.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 4.5 hours
  3. customThe solids were removed via filtration through a pad of Celite
  4. washwere washed with EtOAc
  5. concentrationThe combined filtrates were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-797004f80d3845da8a7dc9337628d0d5
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624927

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