Sodium Carbonate → HCID 68379404, compound

HRID 1410114Notes

Reaction equation

HRID 1410114 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH3:11][C@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11457Benzene, 1-bromo-3-nitro-HCID 6999702(2S)-2-methylpyrrolidineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 68379404HCID 68379404, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-bromo-3-nitrobenzene (1.43 g, 7.06 mmol), (S)-2-methylpyrrolidine (0.5 g, 5.88 mmol), Pd2(dba)3 (0.34 g, 0.59 mmol), X-Phos (0.56 g, 1.18 mmol) and sodium carbonate (1.77 g, 16.74 mmol) in the mixture of 1,4-dioxane (20 mL) and water (20 mL) was heated to reflux for 16 hours. Then water was added, extracted with ethyl acetate and organic layer washed brine dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1) to give (S)-2-methyl-1-(3-nitrophenyl)pyrrolidine (1.1 g, 91%) as red solid. LC-MS: 207 [M+H]+, tR=1.77 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with ethyl acetate and organic layer
  4. washwashed brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1aa099bf04414baeb8e5121fa2a49a4c
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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