Sodium Methoxide → 3-(5-Cyclopropyl-2,4-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one

HRID 1962371Notes

Reaction equation

C[O-].[Na+].CO[C:6]([C:8]1([NH:16][C:17](=[O:30])[CH2:18][C:19]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[C:22]([CH3:28])=[CH:21][C:20]=2[CH3:29])[CH2:13][CH2:12][N:11]([O:14][CH3:15])[CH2:10][CH2:9]1)=[O:7]>CN(C)C=O>[CH:25]1([C:23]2[C:22]([CH3:28])=[CH:21][C:20]([CH3:29])=[C:19]([C:18]3[C:17](=[O:30])[NH:16][C:8]4([CH2:9][CH2:10][N:11]([O:14][CH3:15])[CH2:12][CH2:13]4)[C:6]=3[OH:7])[CH:24]=2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 65 °C

Procedure

To 1.3 g of sodium methoxide in 10 ml of dimethylformamide was added a solution of 3.2 g of crude 4-[2-(5-cyclopropyl-2,4-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester in 10 ml of dimethylformamide and the reaction mixture was heated to 65° C. for 2 hours. The mixture was poured into ice water, extracted with dichloromethane, the combined organic phases dried with sodium sulfate, filtered and concentrated. The residue was subjected to column chromatography (dichloromethane/methanol 95:5) to yield 700 mg of 3-(5-cyclopropyl-2,4-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound C16) as a wax. LC-MS (EI, ES+): 343 (M+H)+

Workup

extractionextracted with dichloromethane
dry with materialthe combined organic phases dried with sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-24a6d87d7f104ab3b7acf6089ef92030
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415369B2

Reaction notes

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