Hydrochloric Acid → (+)-Methyl-1-methyl-5-oxo-3-(2,4,6 trimethoxyphenyl)pyrrolidine-2-carboxylate

HRID 553274Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=2[O:20][CH3:21])[CH2:8][C:7](=[O:22])[NH:6]1)=[O:4].[H-].[Na+].[CH3:25]I.Cl>CN(C)C=O>[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:10]2[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[CH:14][C:15]=2[O:16][CH3:17])[CH2:8][C:7](=[O:22])[N:6]1[CH3:25])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

(+)-Methyl-5-oxo-3-(2,4,6-trimethoxyphenyl)pyrrolidine-2-carboxylate (1.7 g, 0.0055 mol) was dissolved in N,N-dimethylformamide (15 mL) and the solution cooled to 0° C. Sodium hydride (0.134 g, 0.0056 mmol) was added in portions over a period of 10 minutes and stirred for another 20 minutes at 0° C. Methyl iodide (0.514 mL, 0.0082 mol) was added dropwise and the reaction allowed to warm to room temperature in 1 hour. The reaction mixture was poured slowly over a mixture of crushed ice (20 g) and 1:1 hydrochloric acid solution (5 mL). The mixture was extracted with ethyl acetate (2×50 mL), washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to yield an oil. The oil was triturated with petroleum ether and the resulting solid was filtered.

Workup

temperatureto warm to room temperature in 1 hour
extractionThe mixture was extracted with ethyl acetate (2×50 mL)
washwashed with brine
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure
customto yield an oil
customThe oil was triturated with petroleum ether
filtrationthe resulting solid was filtered

Sources & evidence

ORD record: ord-c26afab0edec4cf0bcc5b87c74c776b7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951961B2

Reaction notes

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