Reacción #353205

Ecuación de reacción

NaOH

epichlorohydrin

(3α,5β,7α,12α)-3,7,12-trihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester

→

desired product

Rendimiento 37.0%

(3α,5β,7α,12α)-3-(2,3-epoxypropyl)oxy-7,12-dihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester

Rendimiento 37.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrokept at 0° C.
2. 2
   Otroprepared
3. 3
   workup.ADDITIONWhen the addition
4. 4
   workup.WAITwas left
5. 5
   Otroto react at room temperature by 24 h
6. 6
   OtroThe organic phase was separated
7. 7
   Lavadowashed with H2O to neutral,
8. 8
   Secadodried over Na2SO4
9. 9
   Otroevaporated
10. 10
    OtroThe residue was purified by flash chromatography

Procedimiento

A mixture of 50% NaOH (10 ml), epichlorohydrin (6 ml) and tetrabutylammonium hydrogen sulfate (0.3 g) kept at 0° C. was added drop by drop to a solution of (3α,5β,7α,12α)-3,7,12-trihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester (prepared according to the procedure described by R. P. Bonar-Law et al., J. Chem. Soc. Perkin Trans. I, 1990, 2245) (0.0045 mol) in CH2Cl2 (10 ml). When the addition was completed the mixture was left to react at room temperature by 24 h. The organic phase was separated, washed with H2O to neutral, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography to obtain 0.86 g of desired product (0.0017 mol).

Fuente