Phthalic Anhydride → N-Methyl-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline Phthalimide

HRID 1453972노트

반응식

HRID 1453972 반응식
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:4]([CH3:21])([CH2:5][CH2:6][CH:7]([NH2:20])[CH2:8]2)[CH2:3]1.[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12>C1(C)C=CC=CC=1>[C:22]1(=[O:27])[NH:2][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:4]([CH3:21])([CH2:5][CH2:6][CH:7]([NH2:20])[CH2:8]2)[CH2:3]1

참가 물질

4

반응물 2

HCID 6811Phthalic AnhydrideHCID 68828064N-Methyl-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline

생성물 1

HCID 68828063N-Methyl-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline Phthalimide수율 175.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Amine 20 (1.70 g, 0.0058 mol) was dissolved in anhydrous toluene (100 mL) followed by the addition of phthalic anhydride (2.61 g, 0.018 mol), and the mixture was refluxed with Dean-Stark trap overnight. The solution was then cooled, washed with 1 N NaOH (3×50 mL) and water. The organic layer was collected, dried (Na2SO4) and the solvent removed under reduced pressure yielding crude product. The crude product was purified by flash chromatography (30% EtOAc/hexanes on neutral Al2O3 Brockman activity II-III) to afford 2.22 g (90%) of 21 as a white solid: LCMS (ESI): m/z 419.9 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ 7.80-7.83 [m, 2H], 7.68-7.71 [m, 2H], 7.23-7.27 [m, 3H], 6.77-6.79 [m, 1H], 4.81 [m, 1H], 3.85 [s, 3H], 3.28 [t, J=12 Hz, 1H], 3.01 [d, J=12 Hz, 1H], 2.83-2.85 [m, 1H], 2.65-2.81 [m, 1H], 2.40-2.47 [m, 2H], 2.37 [s, 3H], 2.16-2.20 [m, 1H], 1.89 [ddd, J1=J2=15 Hz, J3=6 Hz, 1H], 1.48-1.58 [m, 3H], 1.33-1.39 [m, 1H], 1.26 [s, 3H]; 13CNMR (CDCl3, 300 MHz) δ 168.8, 159.2, 148.4, 134.1, 132.4, 128.7, 123.3, 121.8, 116.0, 111.0, 64.8, 55.5, 52.9, 47.8, 47.2, 43.8, 36.7, 35.6, 34.1, 26.7, 24.3.

후처리

  1. temperaturethe mixture was refluxed with Dean-Stark trap overnight
  2. temperatureThe solution was then cooled
  3. washwashed with 1 N NaOH (3×50 mL) and water
  4. customThe organic layer was collected
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed under reduced pressure
  7. customyielding crude product
  8. customThe crude product was purified by flash chromatography (30% EtOAc/hexanes on neutral Al2O3 Brockman activity II-III)

출처 및 근거

ORD 기록
ord-a6487c323f2b4c74b1a1758aa5420f5f
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476679B2

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