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 1466143Notes

Reaction equation

HRID 1466143 reaction equation
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

Participants

6

Reactant 4

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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-6916099c4bd04a83aa094c8fd56488be
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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