반응 #614146

반응 방정식

(3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanol

Dess-Martin reagent

→

29b

수율 93.0%

(S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanone

수율 93.0%

용매

CH2Cl2

DCM

반응 조건

후처리

1. 1
   기타reaction
2. 2
   여과The reaction mixture was filtered through a pad of celite
3. 3
   세척the resulting filtrate was washed with 200 mL of aqueous saturated NaHCO3 solution and 200 mL brine
4. 4
   건조The organic phase was dried with MgSO4
5. 5
   여과filtered
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   기타The product was purified by silica gel chromatography (50% EtOAc/hexanes)

실험 절차

To 700 ml DCM solution of 7.9 g (32.16 mmol) (3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanol, 29a, (7.90 g, 32.16 mmol) in CH2Cl2 (700 mL) was added Dess-Martin reagent (17.73 g, 41.81 mmol). The reaction mixture was stirred at room temperature for 20 hours until TLC chromatography indicated reaction was complete. The reaction mixture was filtered through a pad of celite, and the resulting filtrate was washed with 200 mL of aqueous saturated NaHCO3 solution and 200 mL brine. The organic phase was dried with MgSO4, filtered and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography (50% EtOAc/hexanes) to afford 7.3g of the desired product, 29b (93% yield).

출처