Acetonitrile → (R)-3-(3-Hydroxypyrrolidin-1-YL)propanenitrile

(R)-(−)-3-pyrrolidinol hydrochloride (Tokyo Kasei Kogyo Co., Ltd.) (50 g) and potassium carbonate (55.8 g) were dissolved in a mixed solvent of acetonitrile (500 mL) and water (100 mL), and acrylonitrile (29 mL) was added dropwise to the solution at room temperature. Subsequently, the mixture was stirred overnight at room temperature. After the completion of the reaction, the solvent was concentrated, and the obtained residue was dissolved in water. Potassium carbonate was added to saturation. The mixture was extracted 3 times with chloroform, and the extract was dried over potassium carbonate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give (R)-3-(3-hydroxypyrrolidin-1-yl)propionitrile (53 g).

1. additionwas added dropwise to the solution at room temperature
2. customAfter the completion of the reaction
3. concentrationthe solvent was concentrated
4. dissolutionthe obtained residue was dissolved in water
5. additionPotassium carbonate was added to saturation
6. extractionThe mixture was extracted 3 times with chloroform
7. dry with materialthe extract was dried over potassium carbonate
8. concentrationThe solvent was concentrated
9. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

ORD record

ord-a17ebe558cdb4dddab71d9ba06aa34d3

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07459465B2