Reaktion #1111302

Reaktionsgleichung

NaCN

vinyl triflate

5-[3-((S)-2-{4-[1-(4-Methoxy-benzyloxy)-hexyl]-phenyl}-3-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-propyl]-thiophene-2-carboxylic acid methyl ester

→

title compound

Ausbeute 88.0%

5-[3-((S)-3-Cyano-2-{4-[1-(4-methoxy-benzyloxy)-hexyl]-phenyl}-cyclopent-2-enyl)-propyl]-thiophene-2-carboxylic acid methyl ester

Ausbeute 88.0%

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigetransferred to a flask
2. 2
   Waschenrinsing with 1 mL CH3CN
3. 3
   Temperaturcooled to room temperature
4. 4
   Filtrationfiltered through Celite
5. 5
   Waschenwashing with ethyl acetate
6. 6
   WaschenThe filterate was washed with 20 mL water and 20 mL brine
7. 7
   Trocknenwas dried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was purified on a Combiflash unit by Teledyne Isco (4 g silica gel column, 0%→50% ethyl acetate/hexanes)

Vorschrift

A solution of vinyl triflate 48 (61 mg, 0.088 mmol) in 1 mL CH3CN was cannula transferred to a flask containing NaCN (21 mg, 0.42 mmol, dried under vacuum at 105° C. over 3 days), CuI (13 mg, 0.069 mmol), and (Ph3P)4Pd (8 mg, 0.0066 mmol), rinsing with 1 mL CH3CN. The reaction was stirred at 90° C. for 2 h, cooled to room temperature and then filtered through Celite, washing with ethyl acetate. The filterate was washed with 20 mL water and 20 mL brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified on a Combiflash unit by Teledyne Isco (4 g silica gel column, 0%→50% ethyl acetate/hexanes) to give the title compound (41 mg, 88%).

Quelle