Cesium fluoride → HCID 66724999, compound

HRID 1799194Notes

Reaction equation

HRID 1799194 reaction equation
I[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][NH:12][C:11](=[O:14])[CH2:10]1.[CH:15]([Sn](CCCC)(CCCC)CCCC)=[CH2:16].[F-].[Cs+]>CN(C=O)C.O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)=[C:2]([CH:15]=[CH2:16])[CH:7]=1

Participants

8

Reactant 3

HCID 25953Cesium fluorideHCID 81998TributylvinyltinHCID 66724832HCID 66724832, compound

Product 1

HCID 66724999HCID 66724999, compoundYield 87.7%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (4R)-4-(2-iodo-4-chlorophenyl)pyrrolidin-2-one (600 mg, 1.8 mmol), copper(I) iodide (36 mg, 0.18 mmol) and Pd(Ph3P)4 (103 mg, 0.09 mmol) in DMF (5 mL) under a nitrogen atmosphere was introduced vinyl tributyl tin (0.68 g, 2.16 mmol) followed by CsF (54 0 mg, 3.6 mmol). The reaction mixture was heated overnight at 100° C. After the reaction mixture was cooled to room temperature, it was diluted with water and extracted with ethyl ether (3×30 mL). The combined organic phases were washed with a 1N HCl aq. solution, a saturated sodium bicarbonate aqueous solution, and brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo to provide (4R)-4-(4-chloro-2-vinylphenyl)pyrrolidin-2-one (0.35 g, 85% crude yield); MS (ESI) m/z 222.04 (M+H)+. (4R)-4-(4-Chloro-2-vinylphenyl)pyrrolidin-2-one (75 mg, 0.33 mmol) was treated overnight with a 6N HCl aq. solution at 90° C. The product was purified by HPLC to provide the title compound. MS (ESI) m/z 240.06 (M+H)+.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl ether (3×30 mL)
  3. washThe combined organic phases were washed with a 1N HCl aq. solution
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6b07c8f1e17464da535fbed0762a441
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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