Lithium diisopropylamide → 3-(4-Bromo-2-chloro-benzyl)-1-cyclohex-3-enyl-pyrrolidin-2-one

HRID 2235308Notes

Reaction equation

[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[C:24]([Cl:30])[CH:23]=1>C1COCC1>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:9]2[CH2:10][CH2:11][N:7]([CH:1]3[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]3)[C:8]2=[O:12])=[C:24]([Cl:30])[CH:23]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve 1-cyclohex-3-enyl-pyrrolidin-2-one (Preparation 66) (300 mg, 1.82 mmol) in anhydrous THF (8 mL), cool to −78° C. and add LDA (2M in THF, 1.36 mL, 2.72 mmol) dropwise. After 10 minutes add 4-bromo-1-bromomethyl-2-chloro-benzene (512 mg, 1.82 mmol) and allow the mixture to warm to room temperature over 16 h. Quench with saturated aqueous ammonium chloride, extract with dichloromethane, dry the organic layer over sodium sulfate and evaporate. Purify the residue by chromatography on silica gel (eluting 0 to 50% ethyl acetate in hexane) to give the title compound as a clear oil (370 mg, 56%): MS (EI) m/z=367,369 (M+).

Workup

temperatureto warm to room temperature over 16 h
customQuench with saturated aqueous ammonium chloride
extractionextract with dichloromethane
dry with materialdry the organic layer over sodium sulfate
customevaporate
customPurify the residue by chromatography on silica gel (eluting 0 to 50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-e2c5bfd5a73544d0bff2540c26f39e4e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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