Toluene → Tert-butyl1-[4-(2-oxo-pyrrolidin-1-yl)phenyl]cyclopropanecarboxylate

HRID 557826Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C@@H:18]1(N)[CH2:23][CH2:22]CC[C@H:19]1[NH2:24].C(=O)([O-])[O-:27].[K+].[K+].C1(C)C=CC=CC=1>[Cu]I.C(OCC)(=O)C>[O:27]=[C:19]1[CH2:18][CH2:23][CH2:22][N:24]1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 1-(4-bromophenyl)cyclopropanecarboxylate (297.2 mg, 1.0 mmol), t-oxo-pyrrolidine (1.2 mmol), copper(I) iodide (20.0 mg, 0.1 mmol), (trans)-cyclohexane-1,2-diamine (22.8 mg, 0.2 mmol) and potassium carbonate (300.0 mg, 2.17 mmol) was dearated under vacuum and then charged with nitrogen. To the mixture was added toluene (2.0 mL). The resulting mixture was heated at 100° C. for overnight. Then ethyl acetate (10 mL) was added to the mixture. The resulting mixture was filtered through a pad of celite, and the solid was washed with additional ethyl acetate. The filtrate was concentrated. The residue was purified by flash chromatography with ethyl acetate/hexane to afford tert-butyl 1-[4-(2-oxo-pyrrolidin-1-yl)phenyl]cyclopropanecarboxylate.

Workup

additioncharged with nitrogen
filtrationThe resulting mixture was filtered through a pad of celite
washthe solid was washed with additional ethyl acetate
concentrationThe filtrate was concentrated
customThe residue was purified by flash chromatography with ethyl acetate/hexane

Sources & evidence

ORD record: ord-f1209dbdabc143d8b809e92da26cf395
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058288B2

Reaction notes

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