Reaktion #2285195

Reaktionsgleichung

hydrogen

13

5-{3-[(1S,5S)-5-(3-Chloro-5-hydroxymethyl-phenoxymethyl)-4-oxo-cyclopent-2-enyl]-propyl}-thiophene-2-carboxylic acid

→

title compound 15

Ausbeute 30.0%

5-{3-[(1S,2S)-2-(3-Chloro-5-hydroxymethyl -phenoxymethyl)-3-oxo-cyclopentyl]-propyl}thiophene-2-carboxylic acid

Ausbeute 30.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby evacuating
2. 2
   FiltrationThe reaction mixture was filtered through celite
3. 3
   Waschenwashing with EtOAc
4. 4
   Einengenthe filtrate was concentrated in vacuo
5. 5
   SonstigePurification of the resulting crude residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2)

Vorschrift

Palladium on carbon (10 wt. %, 1 mg) was added to a mixture of 12 and 13 (10 mg, ˜0.022 mmol) in EtOAc (0.42 mL). A hydrogen atmosphere was established by evacuating and refilling with hydrogen (10×) and the reaction mixture was stirred under a balloon of hydrogen for 6 h. The reaction mixture was filtered through celite, washing with EtOAc, and the filtrate was concentrated in vacuo. Purification of the resulting crude residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2) afforded 7 mg (˜68%) of ester 14 and 2.7 mg (30%) of title compound 15.

Quelle