Реакция #65954

Уравнение реакции

(R)-8-Fluoro-3-(N-3-pentyl-N-n-propylamino)-5-trifluoromethanesulfonyloxychroman

1,2-bis(diphenylphosphino)propane

DMF

Triethylamine

MeOH

→

(R)-8-fluoro-5-methyloxycarbonyl-3-(N-3-pentyl-N-n-propylamino)chroman

Условия реакции

Обработка

1. 1
   Другоеevaporated to dryness
2. 2
   workup.ADDITION100 ml 2M NH3 and 100 ml EtOAc was added
3. 3
   Экстракцияthe aqueous phase was extracted with 100 ml EtOAc
4. 4
   СушкаThe combined organic layers was dried (MgSO4)
5. 5
   Другоеevaporated

Методика

(R)-8-Fluoro-3-(N-3-pentyl-N-n-propylamino)-5-trifluoromethanesulfonyloxychroman (1.04 g, 2.43 mmol), palladium(II)acetate (55 mg), 1,2-bis(diphenylphosphino)propane (100 mg) was dissolved in 10 ml DMF. Triethylamine (0.75 ml, 5.38 mmol) and MeOH (1.0 ml, 24.6 mmol) was added under CO atm. via septa. The solution was stirred at +70° C. for 18 hours, and thereafter evaporated to dryness. 100 ml 2M NH3 and 100 ml EtOAc was added and the aqueous phase was extracted with 100 ml EtOAc. The combined organic layers was dried (MgSO4) and evaporated. Flash chromatography on silica with a gradient of Hexane-Hexane:EtOAc, 50:1 gave 0.76 g of (R)-8-fluoro-5-methyloxycarbonyl-3-(N-3-pentyl-N-n-propylamino)chroman as an uncoloured oil. Purity: 94% according to GC.

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