Cesium fluoride → 1-[4-(4-Chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one

HRID 1972235Notes

Reaction equation

[F-].[Cs+].[C:3]1([CH:9]2[NH:13][C:12](=[O:14])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:18][CH:17]=1>[Cu](I)I.CNCCNC.C(OCC)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:19]2[CH:28]=[CH:29][C:16]([N:13]3[CH:9]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:10][CH2:11][C:12]3=[O:14])=[CH:17][CH:18]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Step A (Method 2, Using CsF as Base): To a 10 mL reaction tube fitted with a screw cap is charged with 5-phenylpyrrolidin-2-one (80.5 mg, 0.5 mmol), 1-(4-iodophenoxy)-4-chlorobenzene (248 mg, 0.75 mmol, 1.5 eq), copper iodide (5.0 mg, 0.025 mmol, 0.05 eq), CsF (189 mg, 1.25 mmol, 2.5 eq), N1,N2-dimethylethane-1,2-diamine (5.5 μL, 0.05 mmol, 0.1 eq) and ethyl acetate (1 mL). The system is degassed with argon then sealed and heated to 85° C. for 20 h. The reaction is cooled to room temperature, filtered and concentrated in vacuo. Purification on silica gel (0-33% ethyl acetate in hexane) gives 1-[4-(4-chlorophenoxy)phenyl]-5-phenylpyrrolidin-2-one as a colorless oil (182 mg, 100%).

Workup

customfitted with a screw
customcap
customThe system is degassed with argon
customthen sealed
temperatureThe reaction is cooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
customPurification on silica gel (0-33% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-0d1ff09e719445b38301b59a9d0d7147
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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