Реакция #80552

Уравнение реакции

(R)-3-(N-Cyclobutyl-N-n-propylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran

DMF methanol

carbonmonoxide

1,3-bis(diphenylphosphino)propane

triethylamine

→

title compound

Выход 94.0%

Methyl (R)-3-(N-Cyclobutyl-N-n-propylamino)-8-fluoro-3,4-dihydro-2H-1-benzopyran-5-carboxylate

Выход 94.0%

Условия реакции

Обработка

1. 1
   Другоеdegassed
2. 2
   Другоеthe reaction mixture was degassed
3. 3
   Температураto cool
4. 4
   Другоеthe solvent was removed in vacuo
5. 5
   Экстракцияextracted
6. 6
   СушкаThe combined ether portions were dried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Другоеthe solvent removed in vacuo
9. 9
   Другоеto give the crude residue

Методика

(R)-3-(N-Cyclobutyl-N-n-propylamino)-8-fluoro-5-trifluoromethylsulfonyloxy-3,4-dihydro-2H-1-benzopyran (1.00 g, 2.43 mmol) was dissolved in a solution of DMF/methanol (6:2, 20 mL) and then degassed followed by the inlet of carbonmonoxide (×3). With a slight positive pressure of carbonmonoxide, palladium(II)-acetate (18 mg), 1,3-bis(diphenylphosphino)propane (25 mg) and triethylamine (0.75 mL, 5.3 mmol) were added and the reaction mixture was degassed and subjected to carbonmonoxide once again. The reaction was heated to 70° C. under carbonmonoxide atmosphere with vigorous stirring for 6 h. The reaction was allowed to cool and the solvent was removed in vacuo. The remains were taken into a 2M solution of NH3 and then extracted, twice, with diethyl ether. The combined ether portions were dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue. Chromatography on silica (eluent: 15% ethyl acetate/hexane) gave 0.73 mg (94% yield) of the title compound as a clear oil. [α]21D =-130.1° (C=0.1; CHCl3) GC-MS (70 eV) M=321 (2%).

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