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

HRID 1453975ノート

反応式

HRID 1453975 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2320ff759af3459883e14787f0c65bb9
出典データセット
uspto-grants-2009_01
特許番号
US07476679B2

反応ノート

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