Trifluoroacetic acid → 2,2,2-Trifluoro-1-[3-(2-methoxy-benzyl)-azetidin-1-yl]-ethanone

HRID 237299노트

반응식

HRID 237299 반응식
C([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH2:9]1)=O)(C)(C)C.C(O)([C:23]([F:26])([F:25])[F:24])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[F:24][C:23]([F:26])([F:25])[C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH2:9]1)=[O:5]

참가 물질

8

반응물 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 584051693-(2-Methoxy-benzyl)-azetidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 584050552,2,2-Trifluoro-1-[3-(2-methoxy-benzyl)-azetidin-1-yl]-ethanone수율 75%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-(2-methoxy-benzyl)-azetidine-1-carboxylic acid tert-butyl ester (370 mg, 1.3 mmol) in DCM (10 mL) was added TFA (3 mL). After stirring for 16 h, TLC analysis indicated complete consumption of the starting material. To quench the reaction, saturated NaHCO3 solution and EtOAc were added. The aqueous portion was extracted twice with EtOAc and the combined organic extracts were dried (Na2SO4) and concentrated. To a solution of this material in DCM (20 mL) was added triethylamine (370 μL, 2.60 mmol) followed by trifluoroacetic anhydride (204 μL, 1.50 mmol). After 1 h, saturated NaHCO3 solution and EtOAc were added. The aqueous portion was extracted twice with EtOAc and the combined organic extracts were dried (Na2SO4) and concentrated to provide the title compound (274 mg, 75%). MS (ESI): mass calcd. for C13H14F3NO2, 273.1; m/z found, 274.2 [M+H]+. 1H NMR (CDCl3): 7.26-7.20 (m, 1H), 7.07 (dd, J=7.4, 1.6 Hz, 1H), 6.94-6.82 (m, 2H), 4.41 (dd, J=9.6, 8.4 Hz, 1H), 4.23-4.14 (m, 1H), 4.12-4.08 (m, 1H), 3.93-3.84 (m, 1H), 3.82 (s, 3H), 3.18-3.00 (m, 1H), 2.95-2.91 (m, 2H).

후처리

  1. customconsumption of the starting material
  2. customTo quench
  3. customthe reaction, saturated NaHCO3 solution and EtOAc
  4. additionwere added
  5. extractionThe aqueous portion was extracted twice with EtOAc
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. waitAfter 1 h
  9. extractionThe aqueous portion was extracted twice with EtOAc
  10. dry with materialthe combined organic extracts were dried (Na2SO4)
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9b1f4ae216574d95ba92570024951d70
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642583B2

반응 노트

불러오는 중…