Methyl iodide → (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-yl(methyl)carbamate

HRID 529558노트

반응식

HRID 529558 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]1=[O:24].[H-].[Na+].I[CH3:28]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([N:16]([CH3:28])[C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C:10]1=[O:24]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68310539(S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamate

생성물 1

HCID 68310944(S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-yl(methyl)carbamate수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

THF (0.8 mL) was added to a reaction vessel containing (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamate (53 mg, 0.16 mmol). NaH (60% dispersion in oil, 25.4 mg, 0.634 mmol) was then added to the reaction mixture followed by iodomethane (180 mg, 1.27 mmol). The turbid mixture was left to stir at rt for 2 hr. The reaction was quenched by addition of water. The mixture was concentrated to remove some of the THF. The mixture was then partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-yl(methyl)carbamate (52 mg, 0.15 mmol, 94% yield) as a colorless oil.

후처리

  1. waitThe turbid mixture was left
  2. customThe reaction was quenched by addition of water
  3. concentrationThe mixture was concentrated
  4. customto remove some of the THF
  5. customThe mixture was then partitioned between EtOAc and water
  6. customThe organic phase was isolated
  7. washwashed with saturated aqueous NaCl
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9373840662834fe39547364611ad16b7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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