Hydrazine hydrate (1:1) → N-(3-Phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline

HRID 1453975노트

반응식

HRID 1453975 반응식
C1(=O)NC(=O)C2=CC=CC=C12.[C:12]1([CH2:18][CH2:19][CH2:20][N:21]2[CH2:30][CH2:29][C:28]3([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=4)[C:23]([CH3:40])([CH2:24][CH2:25][CH:26]([NH2:39])[CH2:27]3)[CH2:22]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.NN>C(O)C>[C:12]1([CH2:18][CH2:19][CH2:20][N:21]2[CH2:30][CH2:29][C:28]3([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=4)[C:23]([CH3:40])([CH2:24][CH2:25][CH:26]([NH2:39])[CH2:27]3)[CH2:22]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 68827564N-(3-Phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydro-isoquinoline Phthalimide

생성물 1

HCID 68827565N-(3-Phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline수율 97.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Compound 23 (2.00 g, 0.0038 mol) and hydrazine hydrate (1.02 mL, 21.0 mmol) were dissolved in ethanol (100 mL) and refluxed overnight. The solution was then cooled, and the white precipitate was filtered and washed with cold ethanol. The solution was concentrated under reduced pressure and the crude material taken up in 3:1, CH2Cl2/THF (100 mL). The resulting white precipitate was filtered and washed with cold CH2Cl2 (50 mL). The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield crude product. The crude product was purified by flash chromatography (40% CMA 80 in CHCl3) to afford 1.45 g (97%) of 24 as a colorless oil: LCMS (APCI): m/z 393.8 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ 7.14-7.30 [m, 8H], 6.70-6.74 [m, 1H], 3.86 [s, 3H], 3.05 [m, 1H], 2.77-2.79 [br m, 1H], 2.65 [ddd, J1=J2=9 Hz, J3=3 Hz, 2H], 2.58 [d, J=12 Hz, 1H], 2.26-2.36 [m, 4H], 2.04-2.12 [m, 3H], 1.68-1.81 [m, 4H], 1.44-1.50 [m, 4H], 1.32 [m, 1H], 1.21 [s, 3H]; 13C NMR (CDCl3, 300 MHz) δ 159.2, 150.3, 142.9, 128.9, 128.6, 128.5, 126.0, 121.8, 116.5, 110.0, 62.6, 58.2, 55.5, 51.3, 46.9, 44.5, 43.2, 36.7, 36.3, 34.0, 32.1, 29.2, 25.8.

후처리

  1. temperaturerefluxed overnight
  2. temperatureThe solution was then cooled
  3. filtrationthe white precipitate was filtered
  4. washwashed with cold ethanol
  5. concentrationThe solution was concentrated under reduced pressure
  6. filtrationThe resulting white precipitate was filtered
  7. washwashed with cold CH2Cl2 (50 mL)
  8. dry with materialThe combined organic layer was dried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customto yield crude product
  11. customThe crude product was purified by flash chromatography (40% CMA 80 in CHCl3)

출처 및 근거

ORD 기록
ord-2320ff759af3459883e14787f0c65bb9
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476679B2

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