Reacción #1121759

Ecuación de reacción

(R)-2-ethoxycarbonylmethyl-4-triethylsilyloxy-2-cyclopenten-1-one

sodium hydroxide

→

(R)-2-hydroxycarbonylmethyl-4-triethylsiloxy-2-cyclopenten-1-one

Rendimiento 66.2%

Disolventes

phosphate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofinally adjusted to 7.0 upon completion of the reaction
2. 2
   Otrothe Lipase was removed by filtration
3. 3
   ExtracciónThe reaction mixture was extracted with 100 ml of ethyl acetate twice
4. 4
   ExtracciónThe aqueous layer was extracted twice again
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated

Procedimiento

20 g of (R)-2-ethoxycarbonylmethyl-4-triethylsilyloxy-2-cyclopenten-1-one obtained from Example 35 and 2 g of Candida antarcitica lipase were suspended in 200 ml of phosphate buffer (10 mM, pH 6.5-7.5) and stirred at room temperature. The pH of the solution was maintained by 1N sodium hydroxide solution and finally adjusted to 7.0 upon completion of the reaction and the Lipase was removed by filtration. The reaction mixture was extracted with 100 ml of ethyl acetate twice. The pH of the aqueous layer was further adjusted to 6.0 using a saturated sodium hydrogensulfate solution. The aqueous layer was extracted twice again using 100 ml of ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain (R)-2-hydroxycarbonylmethyl-4-triethylsiloxy-2-cyclopenten-1-one (12 g, 65% yield). [α]D: +19.8° (c 1.0, CH3CN);

Fuente