Selenium Dioxide → HCID 178445791, compound

HRID 525463Notes

Reaction equation

[Se](=O)=[O:2].[C:4]([C@H:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([CH3:25])[N:21]=[CH:22]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)([CH3:7])([CH3:6])[CH3:5]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:4]([C@H:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([CH:25]=[O:2])[N:21]=[CH:22]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 200 °C

Procedure

Selenium dioxide (2.25 g, 20.3 mmol) was added to a solution of 7-(trans-4-tert-Butyl-cyclohexyloxy)-3-methyl-isoquinoline (2.01 g, 6.76 mmol) in Diphenyl ether (50 mL, 300 mmol) and the mixture was heated at 200° C. in a sealed tube for 4 hours. The reaction was then cooled to room temperature. Silica gel was added and the flask was placed in a cold water bath to solidify the diphenylether solvent. This solid mixture containing the crude product was purified by flash chromatography to give the title compound in 1.04 g (49%) yield. ESI-MS (M+H+): 312.27

Workup

temperatureThe reaction was then cooled to room temperature
additionSilica gel was added
customthe flask was placed in a cold water bath
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-8cbc40558f23499793b8ac6257b94397
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340527B2

Reaction notes

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