Réaction #10472

Équation de réaction

acetic anhydride

3-[2-(4-fluorophenyl)oxazol-4-ylmethoxyl]cyclohexyl acetate

mono(3-benzyloxycyclohexyl) glutarate

3-benzyloxycyclohexan-1-ol

→

(1R,3S)-3-[2-(4-fluorophenyl)oxazol4-ylmethoxy]cyclohexan-1-ol

Solvants

phosphate

DME

Conditions de réaction

Traitement

1. 1
   workup.WAIT, at 20–23° C. for approx. 20–24 h
2. 2
   ExtractionThe reaction mixture was extracted with dichloromethane
3. 3
   Concentrationconcentrated by evaporation under reduced pressure

Mode opératoire

Approx. 10 mg of 3-[2-(4-fluorophenyl)oxazol-4-ylmethoxyl]cyclohexyl acetate (prepared by reacting 3-benzyloxycyclohexan-1-ol with acetic anhydride, in a similar manner to the synthesis of mono(3-benzyloxycyclohexyl) glutarate see Example 39) were taken up in 2 ml of phosphate buffer (0.1 M, pH=7.0) and 2 ml of DME and stirred with approx. 5 mg of Chirazyme L-2, lyo., at 20–23° C. for approx. 20–24 h. The reaction mixture was extracted with dichloromethane. The organic phase was admixed with toluene and concentrated by evaporation under reduced pressure. The determination of the optical purity for (1R,3S)-3-[2-(4-fluorophenyl)oxazol4-ylmethoxy]cyclohexan-1-ol gave 99.4% ee (HPLC on Chiralpak AD 250×4.6; 1 ml/min, acetonitrile) and 98.9% ee for the (1S,3R)-acetate (HPLC on Chiralcel OD 250×4.6; 1 ml/min, 110:5:1 heptane/EtOH/CH3CN+0.1% TFA).

Source