Iodoethane → HCID 68644205, compound

Temperature

50 °C

Sodium hydride (60% purity, 4.6 g) was suspended in tetrahydrofuran (50 mL) and a solution (50 mL) of (R)-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine (20 g) in tetrahydrofuran was added dropwise under ice-cooling. After the completion of the dropwise addition, the mixture was stirred with heating at 50° C. for 30 min and ice-cooled. Ethyl iodide (18.7 g) was added to the reaction mixture and the mixture was stirred overnight at room temperature. After the completion of the reaction, the solvent was concentrated and water was added to the obtained residue. The mixture was extracted with chloroform and dried over magnesium sulfate. The solvent was concentrated and the obtained residue was purified by silica gel column chromatography. The fraction eluted with hexane:ethyl acetate=3:1 was concentrated to give (R)-1-tert-butoxycarbonyl-2-ethoxymethylpyrrolidine (8.1 g).

1. temperaturecooling
2. additionAfter the completion of the dropwise addition
3. temperatureice-cooled
4. stirringthe mixture was stirred overnight at room temperature
5. customAfter the completion of the reaction
6. concentrationthe solvent was concentrated
7. additionwater was added to the obtained residue
8. extractionThe mixture was extracted with chloroform
9. dry with materialdried over magnesium sulfate
10. concentrationThe solvent was concentrated
11. customthe obtained residue was purified by silica gel column chromatography
12. washThe fraction eluted with hexane
13. concentrationethyl acetate=3:1 was concentrated

ORD record

ord-2855fe5230124776b908ef8152f76bdc

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812178B2