Sodium Bicarbonate → 5-methoxy-3-propyl-3,4-dihydro-2H-pyrrole

HRID 1453911노트

반응식

HRID 1453911 반응식
F[B-](F)(F)F.[CH3:6][O+:7]([CH3:9])C.[CH2:10]([CH:13]1[CH2:17][NH:16]C(=O)[CH2:14]1)[CH2:11][CH3:12].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:6][O:7][C:9]1[CH2:14][CH:13]([CH2:10][CH2:11][CH3:12])[CH2:17][N:16]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 141781004-Propylpyrrolidin-2-one

생성물 1

HCID 229286765-methoxy-3-propyl-3,4-dihydro-2H-pyrrole수율 67.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trimethyloxonium tetrafluoroborate (715 mg, 4.83 mmol) was added to a solution of 4-propyl-2-pyrrolidinone (410 mg, 3.22 mmol) in methylene chloride (8 ml) and the mixture was stirred at room temperature for 14 hours. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture to render it weekly basic and then it was extracted with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the organic layer was subjected to distillation under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (306 mg) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.90 (3H, t, J=7.2 Hz), 1.21-1.50 (4H, m), 2.13 (1H, dd, J=16.4 Hz, 16.8 Hz), 2.34-2.48 (1H, m), 2.57 (1H, dd, J=16.4 Hz, 9.2 Hz), 3.24 (1H, dd, J=13.6 Hz, 6.0 Hz), 3.71-3.90 (4H, m)

후처리

  1. extractionit was extracted with ethyl acetate
  2. washAfter washing the organic layer with brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationthe organic layer was subjected to distillation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-689994f0793a4f85ae6d21d414e6d0df
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476688B2

반응 노트

불러오는 중…