Tetrahydrofuran → 1-Pyrrolidinepropanol

Potassium carbonate (269 g) and pyrrolidine (200 mL) were added in that order to a THF solution (500 mL) of 3-bromopropanol (200 g) at 0° C. The reaction liquid was stirred at room temperature for 15 hours, then ethyl acetate (500 mL) was added to it, and further stirred at room temperature for 1 hour. The obtained reaction liquid was filtered through Celite, and the solid on the Celite was washed with ethyl acetate. The wash liquid and the filtrate were concentrated under reduced pressure, and ethyl acetate (500 mL) was added to the resulting residue, then stirred for 1 hour and filtered through Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified through distillation (boiling point: 62° C., 1 mmHg) to obtain (3-hydroxypropyl)pyrrolidine (156 g, yield 95%).

1. customThe reaction liquid
2. stirringfurther stirred at room temperature for 1 hour
3. customThe obtained reaction liquid
4. filtrationwas filtered through Celite
5. washthe solid on the Celite was washed with ethyl acetate
6. concentrationThe wash liquid and the filtrate were concentrated under reduced pressure, and ethyl acetate (500 mL)
7. additionwas added to the resulting residue
8. stirringstirred for 1 hour
9. filtrationfiltered through Celite
10. concentrationThe filtrate was concentrated under reduced pressure
11. distillationthe resulting residue was purified through distillation (boiling point: 62° C., 1 mmHg)

ORD record

ord-80c4fd38ac1d4ad7b871abcd54c418b8

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790731B2