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Diisopropylamine → HCID 59799081, 화합물

HRID 1013106
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HRID 1013106 반응식
[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[I:26]N1C(=O)CCC1=O>C(Cl)Cl>[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[I:26]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7912DiisopropylamineHCID 120273N-IodosuccinimideHCID 22219609HCID 22219609, 화합물

생성물 1

HCID 59799081HCID 59799081, 화합물수율 65%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
15 °C

실험 절차

Add 6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.037 g, 4.0 mmol) and diisopropylamine (60.7 mg, 0.6 mmol) to anhydrous DCM (350 mL) and stir at 10-20° C. Add slowly a solution of N-iodosuccinimide (1.035 g, 4.6 mmol) in DCM (100 mL) over a period of 3 h. Stir the reaction mixture overnight and gradually warm to RT. Quench the reaction with saturated aqueous sodium bicarbonate, separate the organic layer, wash the organic layer with 0.1 N HCl, brine, dry (sodium sulfate) concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 EtOAc:hexanes) to give the title compound as a white solid (1.0 g, 65%).

후처리

  1. stirringStir the reaction mixture overnight
  2. temperaturegradually warm to RT
  3. customQuench
  4. customthe reaction with saturated aqueous sodium bicarbonate
  5. customseparate the organic layer
  6. washwash the organic layer with 0.1 N HCl, brine
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 5:95 to 10:90 EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-5b0aeb0695894cbba1616769c4fc2c4e
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981882B2

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