Lithium Hydroxide → 1-(2,6-Dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid

HRID 1020984Notes

Reaction equation

C[O:2][C:3]([C:5]1([CH2:19][C:20]([CH3:22])=[CH2:21])[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH2:6]1)=[O:4].[Li+].[OH-]>CO>[CH3:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:18])[C:11]=1[N:7]1[C:8](=[O:10])[CH2:9][C:5]([CH2:19][C:20]([CH3:22])=[CH2:21])([C:3]([OH:4])=[O:2])[CH2:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step a, 10.9 g, 36.21 mmol) in MeOH (100 mL) was added 1M LiOH (100 mL, 100 mmol) and the resulting clear solution was refluxed (70° C.) for an hour. The reaction mixture was then cooled to room temperature, MeOH was removed under reduced pressure and the obtained basic aqueous solution was added to a cooled (0° C.) 2N HCl (200 mL) with vigorous stirring. The resulting white solid was filtered, washed with water (3×300 mL), heptane (200 mL) and dried under high vacuum to obtain 1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid (10 g, quantitative yield). LC-MS: Rt (retention time): 1.98 min, MS: (ES) m/z 288.1 (M+H+).

Workup

temperatureThe reaction mixture was then cooled to room temperature
customMeOH was removed under reduced pressure
additionthe obtained basic aqueous solution was added to
temperaturea cooled (0° C.) 2N HCl (200 mL) with vigorous stirring
filtrationThe resulting white solid was filtered
washwashed with water (3×300 mL), heptane (200 mL)
customdried under high vacuum

Sources & evidence

ORD record: ord-b0ef4dfe882e438688cfe9e89383896d
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716494B2

Reaction notes

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