Reaction #9338

Reaction equation

NaHCO3

15-4

(Z)-7-{(1R,2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

water

THF

→

title compound

Yield 69.8%

(Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

Yield 69.8%

Solvents

acetic acid

Conditions

Workup

1. 1
   Extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
2. 2
   DryingThe combined dichloromethane solution was dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Otherevaporated
5. 5
   OtherThe residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexanes→30% →40%) which

Procedure

A mixture of 15-4 (20 mg, 0.032 mmol) in acetic acid (0.3 mL)/water (0.1 mL)/THF (0.1 mL) was stirred at room temperature. After two days, saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexanes→30% →40%) which gave the title compound (11 mg, 67%).

Source