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-ac64adbf9cba43cfb1422631662cad73

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220759B2