Sodium Methoxide → 3-(2,5-Dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

HRID 1962360Notes

Reaction equation

C[O-].[Na+].C[O:5][C:6]([C:8]1([NH:16][C:17](=[O:27])[CH2:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=2[CH3:26])[CH2:13][CH2:12][N:11]([O:14][CH3:15])[CH2:10][CH2:9]1)=O>CN(C)C=O>[CH3:26][C:20]1[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=1[C:18]1[C:17](=[O:27])[NH:16][C:8]2([CH2:9][CH2:10][N:11]([O:14][CH3:15])[CH2:12][CH2:13]2)[C:6]=1[OH:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To 0.82 g of sodium methylate in 20 ml of dimethylformamide was added a solution of 4-[2-(2,5-dimethyl-phenyl)-acetylamino]-1-methoxy-piperidine-4-carboxylic acid methyl ester in 10 ml of dimethylformamide at a temperature of 60° C. After stirring for 3 hours at 60° C., the reaction mixture was evaporated. The residue was diluted with 10 ml of water, neutralized with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and evaporated to yield 1.23 g of 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound C1) as a light brown resin. This material was triturated with diethyl ether/hexane, filtered and dried to afford a solid, mp: 176-177° C.

Workup

customthe reaction mixture was evaporated
additionThe residue was diluted with 10 ml of water
extractionextracted with ethyl acetate
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-4679bace28174cca9fc6658b4dc19cfb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415369B2

Reaction notes

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