Water → 3-(4-Isopropoxy-3-methyl-benzoyl)-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undec-9-en-8-one

HRID 1478437Notes

Reaction equation

[OH:1][C:2]1([CH2:21][C:22](=[O:32])[CH2:23][C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=O)[CH2:7][CH2:6][N:5]([C:8](=[O:20])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH3:19])[CH:10]=2)[CH2:4][CH2:3]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.O>ClCCl>[CH:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([N:5]2[CH2:6][CH2:7][C:2]3([O:1][C:24]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:23][C:22](=[O:32])[CH2:21]3)[CH2:3][CH2:4]2)=[O:20])=[CH:10][C:11]=1[CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-[4-hydroxy-1-(4-isopropoxy-3-methyl-benzoyl)-4-piperidyl]-1-(3-pyridyl)butane-1,3-dione (1 mmol) in dichloromethane (5 mL) was added PPTS (251 mg, 1.00 mmol). The mixture was heated in microwave at 120° C. for 45 min. Water was added. The aqueous layer was extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by column chromatography (40-50% ethyl acetate-Hex) to provide 3-(4-isopropoxy-3-methyl-benzoyl)-10-(3-pyridyl)-11-oxa-3-azaspiro[5.5]undec-9-en-8-one.

Workup

extractionThe aqueous layer was extracted with dichloromethane (2×)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by column chromatography (40-50% ethyl acetate-Hex)

Sources & evidence

ORD record: ord-aa7c665eaf174e9ab29973db81035450
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403839B2

Reaction notes

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