Di-tert-butyl peroxide → HCID 178445807, compound

HRID 713952Notes

Reaction equation

C([O:5]OC(C)(C)C)(C)(C)C.[Se](=O)=O.[C:14]([C@H:18]1[CH2:23][CH2:22][C@H:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[C:30]([CH3:35])[CH:29]=[CH:28]3)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1.C(Cl)(Cl)Cl>[C:14]([C@H:18]1[CH2:23][CH2:22][C@H:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[C:30]([CH:35]=[O:5])[CH:29]=[CH:28]3)[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

Di-tert-butyl peroxide (1.93 mL, 10.5 mmol) was added to a suspension of Selenium dioxide (2.68 g, 24.1 mmol) in 1,4-Dioxane (24.00 mL, 307.5 mmol). The mixture was stirred for 30 minutes, then 6-(trans-4-tert-Butyl-cyclohexyloxy)-2-methyl-quinoline (3.12 g, 10.5 mmol) was added as a solution in 1,4-Dioxane and the mixture was heated overnight at 50° C. The reaction mixture was then cooled to room temperature, diluted in chloroform and filtered through a pad of celite. The filtrate was washed with water. The layers were separated and the combined organic phase was dried over MgSO4, filtered, concentrated under reduced pressure, adsorbed onto silica gel and purified by flash chromatography (0-30% EtOAc in hexanes) to give the title compound as a pale yellow solid in 20% yield. ESI-MS (M+H+): 312.27.

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered through a pad of celite
washThe filtrate was washed with water
customThe layers were separated
dry with materialthe combined organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by flash chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7578df9ad83d440fb7bd27f12fa4ff46
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186367B2

Reaction notes

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