4-Nitrophenol → 1-(2-(4-Nitrophenoxy)ethyl)pyrrolidine

HRID 2189268Notes

Reaction equation

HRID 2189268 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[N+:34]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)([O-:36])=[O:35].O[CH2:45][CH2:46][N:47]1[CH2:51][CH2:50][CH2:49][CH2:48]1>C1COCC1>[N+:34]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:45][CH2:46][N:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)=[CH:39][CH:38]=1)([O-:36])=[O:35]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 4198581-(2-(4-Nitrophenoxy)ethyl)pyrrolidineYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of PPh3 (866 mg, 3.3 mmol) in THF (6 mL) is added DIAD (0.65 mL, 3.3 mmol) at 0° C. The suspension was stirred for 10 minutes, then heated to room temperature. To the mixture, 4-nitrophenol (460 mg, 3.3 mmol) and 1-(2-hydroxyethyl)-pyrrolidine (0.26 mL, 2.2 mmol) is added, and the mixture is stirred at room temperature for 16 hours, then concentrated. The residue is taken up in EtOAc, washed with 1N NaOH aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=1:99 to 10:90) to give 277 mg of 1-[2-(4-Nitro-phenoxy)-ethyl]-pyrrolidine as a white solid.

Workup

  1. stirringthe mixture is stirred at room temperature for 16 hours
  2. concentrationconcentrated
  3. washwashed with 1N NaOH aqueous solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography (SiO2, MeOH:CH2Cl2=1:99 to 10:90)

Sources & evidence

ORD record
ord-b7a8772e9ef5499f8abf258345646411
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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