Reacción #9334

Ecuación de reacción

9-1

(Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-hydroxymethyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester

NMO

→

9-2

Rendimiento 79.7%

(Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-formyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester

Rendimiento 79.7%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITfor 1 h at room temperature
2. 2
   FiltraciónThe mixture was then filtered through a pad of silica gel
3. 3
   Lavadowashing with ethyl acetate
4. 4
   OtroThe solvents were evaporated
5. 5
   Otrothe residue was purified by flash chromatography on silica gel (10% ethyl acetate/hexanes)

Procedimiento

An ice cold mixture of 9-1 (43 mg, 0.089 mmol), 4 Å molecular sieves (56 mg) and NMO (16 mg, 0.14 mmol) in dichloromethane (0.5 mL) was treated with TPAP (3 mg, 0.009 mmol). The mixture was stirred for 5 min. at 0° C. and then for 1 h at room temperature. The mixture was then filtered through a pad of silica gel, washing with ethyl acetate. The solvents were evaporated and the residue was purified by flash chromatography on silica gel (10% ethyl acetate/hexanes) to give 9-2 (34 mg, 79%).

Fuente