반응 #454276

반응 방정식

ethyl p-toluenesulfonate

5-hydroxy-3-(1-Boc-2-(S)-azetidinylmethoxy)pyridine

KOH

→

title compound

수율 98.0%

5-Ethoxy-3-(1-Boc-2-(S)-azetidinylmethoxy)pyridine

수율 98.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe resultant was stirred at 80° C. overnight
2. 2
   농축The mixture was concentrated
3. 3
   기타to remove the dimethylformamide
4. 4
   workup.ADDITIONthe residue was diluted with water
5. 5
   추출extracted with EtOAc
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated under vacuum
9. 9
   기타to give 1.0 g of unpurified product
10. 10
    기타This material was purified by chromatography (silica gel: hexane/EtOAc, 1:1)

실험 절차

A solution of 5-hydroxy-3-(1-Boc-2-(S)-azetidinylmethoxy)pyridine (500 mg, 1.78 mmol, from step 120f) in dimethylformamide (15 mL) was treated with ground KOH (170 mg, 1.7 mmol) and stirred for 30 minutes at room temperature. To this mixture was rapidly added ethyl p-toluenesulfonate (430 mg, 2.14 mmol), and the resultant was stirred at 80° C. overnight. The mixture was concentrated to remove the dimethylformamide, and the residue was diluted with water and extracted with EtOAc. The organic extracts were combined, dried (MgSO4), filtered and concentrated under vacuum to give 1.0 g of unpurified product. This material was purified by chromatography (silica gel: hexane/EtOAc, 1:1) to give 537 mg (98%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ: 1.40 (s, 9H), 1.42 (t, J=6 Hz, 3H), 2.30 (m, 2H), 3.92 (t, J=9 Hz, 2H), 4.05 (q, J=6 Hz, 2H), 4.30 (m, 1H), 4.54 (m, 1H), 6.80 (m, 1H), 7.95 (m, 2H). MS (CI/NH3) m/e: 309 (M+H)+.

출처