Réaction #80566

Équation de réaction

(R)-3-(N-Cyclopentyl-N-cyclobutylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran

triethylamine

methanol

DMF

carbon monoxide

→

title compound

Methyl (R)-3-(N-Cyclopentyl-N-cyclobutylamino)-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxylate

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in diethyl ether
3. 3
   workup.ADDITIONtreated with active charcoal
4. 4
   AutreEvaporation of the solvent

Mode opératoire

(R)-3-(N-Cyclopentyl-N-cyclobutylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran (0.67 g, 1.5 mmol) (4), DMF (20 mL), triethylamine (0.6 g, 6 mmol), methanol (0.8 g, 12.7 mmol), palladium(II)acetate (22 mg, 0.1 mmol) and 1,3-bis(diphenylphosphino)propane (44 mg, 0.1 mmol) were placed in a round-bottomed flask. The solution was stirred at 75° C. in an atmosphere of carbon monoxide for 4 h. The solvent was removed in vacuo, the residue was dissolved in diethyl ether and treated with active charcoal. Evaporation of the solvent afforded 380 mg of the title compound as an uncolored oil. GC/MS (70 eV) M=347 (3 %).

Source