3-(3-METHOXYPHENYL)PYRROLIDINE Chemical Properties

Boiling point:

92-94 °C(Press: 0.3 Torr)

Density 

1.024±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

10.13±0.10(Predicted)

3-(3-METHOXYPHENYL)PYRROLIDINE Usage And Synthesis

Synthesis

To an oven-dried three-neck flask was added 4-(3-methoxyphenyl)pyrrolidin-2-one (3.66 g, 19.2 mmol) and anhydrous THF (50 mL). The reaction mixture was cooled to 0 °C (ice-salt bath) and a THF solution of LiAlH4 (2.4 M, 16.0 mL, 38.4 mmol) was added slowly and dropwise. After the reaction mixture was gradually warmed to room temperature, it was heated to reflux at 65 °C for 2 hours. Upon completion of the reaction, the mixture was cooled again to 0 °C (ice-salt bath) and 0.5 M NaOH solution (~4.5 mL) was added slowly and dropwise to quench the reaction. The quenched mixture was filtered through a diatomaceous earth pad (7-8 cm) and the filter cake was washed with CH2Cl2 (200 mL). The combined organic phases were dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by simple distillation (Kugelrohr, 100 °C, 2.7 mmHg) to afford racemic 3-(3-methoxyphenyl)pyrrolidine (2.60 g, 77% yield) as a colorless oil. The product was confirmed by 1H NMR, 13C NMR, LCMS and HRMS analysis.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1897 - 1902

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