Reaktion #83935

Reaktionsgleichung

potassium carbonate

racemic tosylate

6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole

→

Racemic 3-hydroxybutyl tosylate

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was warmed
2. 2
   Temperaturto reflux for 4.5 hours
3. 3
   SonstigeThe solids were removed via filtration through a pad of Celite
4. 4
   Waschenwere washed with EtOAc
5. 5
   EinengenThe combined filtrates were concentrated

Vorschrift

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.

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