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Methanol → (1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine

HRID 501688
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HRID 501688 반응식
[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C@@H:7]([NH:16]C(=O)C(F)(F)F)[CH2:6]1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C@@H:7]([NH2:16])[CH2:6]1)[CH:2]=[CH2:3]
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참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 58813111N-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide

생성물 1

HCID 59676150(1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine수율 87.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Step U (2): N-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide (1.28 g, 4.06 mmol) from Step U (1), potassium carbonate (2.85 g, 20.8 mmol) and MeOH (92 mL)/H2O (6 mL) were heated at reflux for 16 h. The reaction mixture was concentrated in vacuo. Added water to the residue, extracted with EtOAc, washed the organic layers with brine, dried over Na2SO4, filtered and concentrated to afford 780 mg (quantitative yield) of the title compound as light brown oil. HRMS (M+H)+=220.1336; [α]D +18.72 (c=8.86 mg/mL, ethanol) 1H NMR (500 MHz, CDCl3) δ ppm 1.66 (s, 1H) 1.76 (d, J=12.82 Hz, 1H) 2.74-2.83 (m, 1H) 3.81 (s, 3H) 4.04-4.18 (m, 3H) 4.77 (t, J=5.80 Hz, 1H) 5.18 (dd, J=10.38, 1.53 Hz, 1H) 5.32 (dd, J=17.24, 1.68 Hz, 1H) 5.97 (dd, 1H) 6.90 (d, J=2.44 Hz, 1H) 7.30 (d, J=8.24 Hz, 1H).

후처리

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionAdded water to the residue, extracted with EtOAc
  4. washwashed the organic layers with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7301532b375c4c9b9e84d7d4167f0db7
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772221B2

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