Trifluoroacetic acid → 3-(azetidin-3-yloxy)pyridine

HRID 2180244노트

반응식

HRID 2180244 반응식
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:11]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 24902674HCID 24902674, 화합물

생성물 1

HCID 102195283-(azetidin-3-yloxy)pyridine수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 160 mg (0.64 mmol) of 3-(1-t-butoxycarbonyl-3-azetidinyloxy)-pyridine was added 6 mL of solution containing 3 mL of TFA and 3 mL of CH2Cl2 at ice-bath temperature. The reaction solution was slowly warmed to room temperature and allowed to stir 50 min at room temperature. After 50 min, solvents were removed in vacuo and the crude product was purified by flash chromatography (9:1: 0.05, CHCl3: MeOH:conc. NH4OH) to obtain 62 mg (67%) of a white solid: 1H NMR (300 MHz, CD3OD) δ 8.23 (2H, br s), 7.38 (2H, br d), 5.24 (2H, br s), 4.58 (2H, br d), 4.20 (2H, br d, J=9.8 Hz); Mass spectrum (ESI) m/z 151.7 (M+H+).

후처리

  1. waitAfter 50 min
  2. customsolvents were removed in vacuo
  3. customthe crude product was purified by flash chromatography (9:1: 0.05, CHCl3: MeOH:conc. NH4OH)

출처 및 근거

ORD 기록
ord-b632f9a39d7848d792d00150d77d8583
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06888001B2

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