Methyl iodide → benzyl N-[(3R)-2-methylsulfanyl-4,5-dihydro-3H-1-benzazepin-3-yl]carbamate

HRID 2068542노트

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HRID 2068542 반응식
[S:1]=[C:2]1[C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[NH:3]1.[H-].[Na+].[CH3:26]I>C1COCC1>[CH3:26][S:1][C:2]1[C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH2:6][C:5]2[CH:20]=[CH:21][CH:22]=[CH:23][C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58304042benzyl N-[(3R)-2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate

생성물 1

HCID 58304100benzyl N-[(3R)-2-methylsulfanyl-4,5-dihydro-3H-1-benzazepin-3-yl]carbamate수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Dissolve benzyl N-[(3R)-2-thioxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]carbamate (1.5 g, 4.60 mmol) in THF (40 mL), cool to 0° C., and add sodium hydride (NaH) (192.9 mg, 4.83 mmol, 60% in mineral oil) all at once. Remove the bath and stir the reaction for approximately 1 hour under nitrogen. Add methyl iodide (300 μL, 4.83 mmol) and stir for approximately 1 hour at ambient temperature. Concentrate the reaction under reduced pressure to remove most of the THF, dilute the residue with ethyl acetate, and wash with saturated sodium bicarbonate and brine, dry over sodium sulfate, and concentrate the organic layers under reduced pressure to give the title compound (1.5 g, 96%) as a white solid: MS (m/z): 341 (M+1).

후처리

  1. customRemove the bath
  2. customthe reaction for approximately 1 hour under nitrogen
  3. concentrationConcentrate
  4. customthe reaction under reduced pressure
  5. customto remove most of the THF
  6. additiondilute the residue with ethyl acetate
  7. washwash with saturated sodium bicarbonate and brine
  8. dry with materialdry over sodium sulfate
  9. concentrationconcentrate the organic layers under reduced pressure

출처 및 근거

ORD 기록
ord-d2ea9ec165eb4034970292d74032b292
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299061B2

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