Cesium carbonate → 2-(Methoxymethyl)-1-(3-nitrophenyl)pyrrolidine

HRID 1410048Notes

Reaction equation

HRID 1410048 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][O:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>[CH3:11][O:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 11457Benzene, 1-bromo-3-nitro-HCID 1439532-(Methoxymethyl)pyrrolidine

Product 1

HCID 683792402-(Methoxymethyl)-1-(3-nitrophenyl)pyrrolidineYield 72%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1-bromo-3-nitrobenzene (300 mg, 1.48 mmol), 2-(methoxymethyl)pyrrolidine (187 mg, 1.63 mmol), Cs2CO3 (800 mg, 2.45 mmol), X-Phos (50 mg, 0.1 mmol), Pd(dba)2 (50 mg, 0.087 mmol) in 50 mL of dioxane were stirred at reflux overnight under N2 atmosphere. The excess of dioxane was removed under reduced pressure and the residue was purified by silica gel chromatography, eluting with a mixture of petroleum ether and ethyl acetate (5:1) to give 2-(methoxymethyl)-1-(3-nitrophenyl)pyrrolidine (250 mg, 72%) as a yellow solid. LC-MS: 237 [M+H]+, tR=1.71 min.

Workup

  1. temperatureat reflux overnight under N2 atmosphere
  2. customThe excess of dioxane was removed under reduced pressure
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with a mixture of petroleum ether and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-946ddf9cf8754a7cb133fc1d6a324bca
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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