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Diisopropylamine → HCID 59799081, 화합물

HRID 911233
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HRID 911233 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

반응 조건

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 ambient temperature. Quench the reaction with saturated aqueous NaHCO3, separate the organic layer, wash the organic layer with 0.1N aqueous HCl, brine, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:20 to 1:10) to give the desired intermediate as a white solid (1.0 g, 65%). MS (ES+) m/z: 386 (M+H)+.

후처리

  1. stirringStir the reaction mixture overnight
  2. temperaturegradually warm to ambient temperature
  3. customQuench
  4. customthe reaction with saturated aqueous NaHCO3
  5. customseparate the organic layer
  6. washwash the organic layer with 0.1N aqueous HCl, brine
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:20 to 1:10)

출처 및 근거

ORD 기록
ord-6a020f94b10c489bbac4210a5debe708
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022062B2

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