Methyl 4-(4-bromophenyl)-4-(hydroxyimino)butanoate → 5-(4-Bromophenyl)pyrrolidin-2-one

HRID 2188940Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:15]O)[CH2:9][CH2:10][C:11](OC)=[O:12])=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:15][C:11](=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of methyl 4-(4-bromophenyl)-4-(hydroxyimino)butanoate (5.0 g, 17 mmol) in acetic acid (60 mL) was added Zn (2.3 g, 35 mmol). The resulting mixture was stirred at 80° C. overnight under N2 atmosphere. The reaction was cooled to room temperature and filtered. The filtrate was neutralized with saturated NaHCO3 solution and extracted with ethyl acetate (30 mL×3). The combined organics were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The solid was washed with ether to afford 5-(4-bromophenyl)-pyrrolidin-2-one (0.82 g, 20%). 1H NMR (CDCl3, 400 MHz) δ 7.50 (d, J=8.4, 1H), 7.18 (d, J=8.4, 2H), 5.87 (br s, 1H), 4.72 (t, J=6.8, 2H), 2.63-2.50 (m, 1H), 2.48-2.38 (m, 2H), 1.98-1.89 (m, 1H). MS (ESI) m/z 240.1 [M+H+].

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
extractionextracted with ethyl acetate (30 mL×3)
washThe combined organics were washed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
washThe solid was washed with ether

Sources & evidence

ORD record: ord-e3caf9fd646e4bf195ed2b0e8316e870
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324207B2

Reaction notes

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