Reaction #9332

Reaction equation

HF-pyridine

chloride

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

→

diol

(Z)-7-{(1R,2S,3R,5R)-5-Chloro-2-[4-(cyclohexyl-hydroxy-methyl)-phenyl]-3-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

Solvents

CH3CN

Conditions

Workup

1. 1
   Otherwas quenched by addition of saturated NaHCO3 solution
2. 2
   ExtractionThe mixture was extracted with dichloromethane (3×30 mL)
3. 3
   Dryingthe combined dichloromethane solution dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherPurification by flash chromatography on silica gel (20% ethyl acetate/hexanes)

Procedure

HF-pyridine (0.60 mL) was added to a 0° C. CH3CN solution of chloride 6-2 (24 mg, 20%) and the mono TBS derivative (36 mg, 36%). The reaction was stirred for 1 h, and then was quenched by addition of saturated NaHCO3 solution. The mixture was extracted with dichloromethane (3×30 mL) and the combined dichloromethane solution dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (20% ethyl acetate/hexanes) gave the title diol 6-3 (37 mg, 93%).

Source