Methanol → (S)-4-([1,4]oxazepan-6-yl)benzonitrile

HRID 515466노트

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HRID 515466 반응식
C1([C@H]([N:9]2[CH2:15][C@H:14]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH2:13][O:12][CH2:11][CH2:10]2)C)C=CC=CC=1.ClC(OC(Cl)C)=O.CO>ClCCCl>[O:12]1[CH2:13][C@@H:14]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH2:15][NH:9][CH2:10][CH2:11]1

참가 물질

5

반응물 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67283020(S)-4-(4-((R)-1-phenylethyl)-[1,4]oxazepan-6-yl)benzonitrile

생성물 1

HCID 67281424(S)-4-([1,4]oxazepan-6-yl)benzonitrile수율 71.4%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of (S)-4-(4-((R)-1-phenylethyl)-[1,4]oxazepan-6-yl)benzonitrile (0.662 g, 2.16 mmol) in 1,2-dichloroethane (3.60 ml) was added 1-chloroethyl chloroformate (0.772 g, 5.40 mmol) at room temperature. The mixture was refluxed for 8 hours. Methanol (15 ml) was added to the mixture cooled to room temperature. The mixture was refluxed again for 2 hours. The mixture was concentrated in vacuo. The residue was partitioned between aqueous sodium hydrogen carbonate and chloroform. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=96/4) to afford (S)-4-([1,4]oxazepan-6-yl)benzonitrile as pale yellow solid (312 mg, 70%).

후처리

  1. temperatureThe mixture was refluxed for 8 hours
  2. temperatureThe mixture was refluxed again for 2 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was partitioned between aqueous sodium hydrogen carbonate and chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=96/4)

출처 및 근거

ORD 기록
ord-11a78b63f71d4cea9be8990abc8f54c6
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108957B2

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