Triphenylphosphine → 1-[2-(4-Bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidine

HRID 1514881Notes

Reaction equation

HRID 1514881 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[N:11]1([CH2:16][CH2:17]O)[CH2:15][CH2:14][CH2:13][CH2:12]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:17][CH2:16][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 762881-PyrrolidineethanolHCID 819704-Bromo-3,5-dimethylphenolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 669656511-[2-(4-Bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidine

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (555 mg) were added 2-pyrrolidine-1-yl-ethanol (0.3 mL), PPh3 (721 mg), and DEAD (0.43 mL). The mixture was stirred room temperature for 16 h. The reaction mixture was concentrated. The residue was treated with Et2O, filtered and the filtrated was concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=10:80 to 80:20) to give 1-[2-(4-bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidine as a white solid: MS (m/z) 300 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was treated with Et2O
  3. filtrationfiltered
  4. concentrationthe filtrated was concentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=10:80 to 80:20)

Sources & evidence

ORD record
ord-624febe23e2e4b6f98f8a93dd697df10
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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