Water → 8-Benzyloxy-1-(3,4-dimethoxy-benzyl)-7-methoxy-2,3,4,5-tetrahydro-1H benzo[c]azepine

HRID 458791노트

반응식

HRID 458791 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=O)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[CH:11][C:10]=1[O:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.[BH4-].[Na+].O>C(#N)C.C(Cl)Cl.CO>[CH2:1]([O:8][C:9]1[C:10]([O:32][CH3:33])=[CH:11][C:12]2[CH2:15][CH2:16][CH2:17][NH:18][CH:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[C:13]=2[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 18442596N-[3-(4-Benzyloxy-3-methoxy-phenyl)-propyl]-2-(3,4-dimethoxy-phenyl)-acetamide

생성물 1

HCID 184425878-Benzyloxy-1-(3,4-dimethoxy-benzyl)-7-methoxy-2,3,4,5-tetrahydro-1H benzo[c]azepine

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 21226129Dichloromethane methanol용매

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온도
0 °C

실험 절차

A mixture of N-[3-(4-benzyloxy-3-methoxy-phenyl)-propyl]-2-(3,4-dimethoxy-phenyl)-acetamide (6.04 g, 13.43 mmol) and POCl3 (4.1 ml, 44.78 mmol) in anhydrous acetonitrile (350 ml) was stirred at reflux for 5 h under nitrogen. After cooling, the reaction mixture was concentrated in vacuo and the residue was dissolved in MeOH (120 ml). The solution was cooled to 0° C. and NaBH4 (3.50 g, 92.70 mmol) was added portionwise. After stirring at 0° C. for 2 h under nitrogen, the reaction mixture was poured into H2O and extracted three times with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (CH2Cl2/MeOH: 9/1) gave the title compound as a racemic mixture (2.44 g, 5.62 mmol, 42%, yellow oil).

후처리

  1. temperatureat reflux for 5 h under nitrogen
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in MeOH (120 ml)
  5. stirringAfter stirring at 0° C. for 2 h under nitrogen
  6. extractionextracted three times with CH2Cl2
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a crude oil

출처 및 근거

ORD 기록
ord-addeb4ec1546413f88dab49649a8ec33
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192950B2

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