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

HRID 412196노트

반응식

HRID 412196 반응식
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 10801570tert-Butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate

생성물 1

HCID 101542053-(Pyrrolidin-3-yloxy)pyridine수율 30.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 1.3 gm of 3-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-pyridine was added 10 mL of solution containing 5 mL of TFA and 5 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 120 mg (30.4% yield in two steps) of a clear oil: 1H NMR (300 MHz, CD3OD) δ8.21 (1H, d, J=2.6 Hz), 8.11 (1H, d, J=4.7 Hz), 7.38 (2H, m), 5.00 (1H, m), 3.13-2.88 (4H, m), 2.20-1.95 (2H, m); Mass spectrum (ESI) m/z 165.6 (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)
  4. customto obtain 120 mg (30.4% yield in two steps) of a clear oil

출처 및 근거

ORD 기록
ord-0c39ab77737443c1bb8ef5d05201d4ca
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562847B1

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