Pyrrolidine → 3-Pyrrolidinophenethyl Alcohol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-bromophenethoxy)tetrahydro-2H-pyran (6.27 g, 21.9 mmol) in toluene (15 ml) and pyrrolidine (2.2 ml, 26.4 mmol) were added to a mixture of dry palladium acetate (58 mg, 0.26 mmol), 2-(di-t-butylphosphino)biphenyl (136 mg, 0.46 mmol) and sodium t-butoxide (3.23 g, 33.6 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 the product was extracted with ethyl acetate. The organic layer was dried to quantitatively obtain 3-pyrrolidinophenethyl alcohol in the form of a light yellow solid.

Provenance & Evidence