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Ozone → 6-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466143
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HRID 1466143 반응식
O=[O+][O-].[CH2:4]([C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[CH:8]=1)[CH:5]=C.[O:17]=[C:18]1[CH2:23][NH:22][CH2:21][CH2:20][N:19]1[CH:24]1[CH2:33][CH2:32][C:31]2[CH:30]=[C:29]([C:34]#[N:35])[CH:28]=[CH:27][C:26]=2[CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[O:17]=[C:18]1[CH2:23][N:22]([CH2:5][CH2:4][C:7]2[CH:16]=[CH:15][C:10]3[C:11](=[O:14])[O:12][CH2:13][C:9]=3[CH:8]=2)[CH2:21][CH2:20][N:19]1[CH:24]1[CH2:33][CH2:32][C:31]2[CH:30]=[C:29]([C:34]#[N:35])[CH:28]=[CH:27][C:26]=2[CH2:25]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 24823OzoneHCID 5049666Sodium triacetoxyborohydrideHCID 666439845-allyl-2-benzofuran-1(3H)-oneHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

생성물 1

HCID 715195886-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Ozone was bubbled into a solution of 5-(prop-2-en-1-yl)-2-benzofuran-1(3H)-one (102 mg, 0.59 mmol) in DCM until the color changed to orange. Excess ozone was removed by bubbling nitrogen through the reaction, which was followed by addition of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (50 mg, 0.20 mmol) and sodium triacetoxyborohydride (210 mg, 0.98 mmol). The reaction was allowed to stir at RT for 24 hours. The reaction was diluted with DCM, washed with brine, dried over MgSO4, and purified by prep-TLC to afford the title product. LC-MS (IE, m/z): 416 [M+1]+.

후처리

  1. customExcess ozone was removed
  2. customby bubbling nitrogen
  3. customthrough the reaction, which
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. custompurified by prep-TLC

출처 및 근거

ORD 기록
ord-6916099c4bd04a83aa094c8fd56488be
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08999990B2

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