Pyrrolidine → 2-[4-(Pyrrolidin-1-yl)phenyl]ethan-1-ol

HRID 2251885Notes

Reaction equation

HRID 2251885 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH2:7][O:8]C2CCCCO2)=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N:17]1([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][OH:8])=[CH:15][CH:16]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 31268PyrrolidineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 133067582-[2-(4-Bromophenyl)ethoxy]oxaneHCID 23676156Sodium t-butoxide

Product 1

HCID 124983722-[4-(Pyrrolidin-1-yl)phenyl]ethan-1-ol

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(4-bromophenethoxy)tetrahydro-2H-pyran (28.01 g, 98.39 mmol) in toluene (100 ml) and pyrrolidine (9.93 ml, 119 mmol) were added to a mixture of dry palladium acetate (270 mg, 1.20 mmol), 2-(di-t-butylphosphino)biphenyl (720 mg, 2.40 mmol) and sodium t-butoxide (14.42 g, 150 mmol), and they were stirred at 70° C. for 12 hours. Water was added to the reaction mixture. After the extraction with ethyl acetate, the product was extracted from the organic layer with 1 M hydrochloric acid. The aqueous layer was neutralized with an aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried to obtain 4-pyrrolidinophenethyl alcohol in the form of a light yellow solid (16.41 g, 87%).

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. extractionthe product was extracted from the organic layer with 1 M hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried

Sources & evidence

ORD record
ord-a165be94446c4c7e8ea5db701985342d
Source dataset
uspto-grants-2008_01
Patent number
US07320973B2

Reaction notes

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