Sodium Methoxide → Methyl 1-benzyl-2,2-dimethyl-4,5-dioxopyrrolidine-3-carboxylate

HRID 1366613Notes

Reaction equation

[CH3:1][C:2]([N:9]([C:17](=[O:22])[C:18](OC)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C[O-].[Na+]>C1(C)C=CC=CC=1.CO>[CH3:1][C:2]1([CH3:8])[CH:3]([C:4]([O:6][CH3:7])=[O:5])[C:18](=[O:19])[C:17](=[O:22])[N:9]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl 3-methyl-3-[[(methyloxy)(oxo)acetyl](phenylmethyl)amino]butanoate (6.9702 g, 22.68 mmol) in toluene (110 mL) was added 25% w/w NaOMe in MeOH (14 mL). The mixture was heated at 80° C. and stirred for 2 h. The solution was then cooled to room temperature and concentrated in vacuo to ca. ½ volume. The residue was partitioned between DCM (200 mL) and 1 N aq. HCl (200 mL). The aqueous phase was extracted with a fresh portion of DCM (100 mL), and the combined organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The resulting white solid was triturated with hexanes and collected by vacuum filtration to afford methyl 2,2-dimethyl-4,5-dioxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate (5.5965 g, 88%) as a white solid. LCMS: (M+H)+: 276.1.

Workup

temperatureThe solution was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was partitioned between DCM (200 mL) and 1 N aq. HCl (200 mL)
extractionThe aqueous phase was extracted with a fresh portion of DCM (100 mL)
dry with materialthe combined organic phase was dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting white solid was triturated with hexanes
filtrationcollected by vacuum filtration

Sources & evidence

ORD record: ord-8aecdd6b886e46d18cd8a9b5e2112e92
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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