4-Chloroanisole → Pyrrolidine, 1-(4-methoxyphenyl)-

HRID 1937795Notes

Reaction equation

HRID 1937795 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.CC([O-])(C)C.[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].C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 121674-ChloroanisoleHCID 31268PyrrolidineHCID 23676156Sodium t-butoxide

Product 1

HCID 143187Pyrrolidine, 1-(4-methoxyphenyl)-Yield 95%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

An oven dried test tube was charged with Pd2(dba)3 (4.5 mg, 0.005 mmol), 27 (7.4 mg, 0.015 mmol), 4-chloroanisole (140 mg, 0.98 mmol), pyrrolidine (85 mg, 1.2 mmol), NaOt-Bu (135 mg, 1.4 mmol), toluene (2 mL), and purged with argon. The mixture was heated to 80° C. and stirred for 18 hours. The reaction mixture was cooled to room temperature, diluted with ether (5 mL), filtered through a plug of celite, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give 165 mg (95%) of the title product as colorless crystals.

Workup

  1. customAn oven dried test tube
  2. custompurged with argon
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with ether (5 mL)
  5. filtrationfiltered through a plug of celite
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-59e8788eff4549079a75da623ceedca9
Source dataset
uspto-grants-2002_05
Patent number
US06395916B1

Reaction notes

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