HCID 22871819, compound → HCID 45087015, compound

1-Benzyl-4-(R)-methyl-3-(R)-[(4-(S)-phenyl-2-oxazolidinon-3-yl)carbonyl]pyrrolidine (150 g) was dissolved in cyclopropylamine (650 mL). The mixture was stirred at room temperature for 23 hours and was concentrated under reduced pressure. Diisopropyl ether (800 mL) was added to the residue and the solution was stirred at room temperature for 70 min. The resulting crystals were filtered. The collected crystals were then dissolved in dichloromethane (800 ml) and the solution was extracted with 1 mol/L hydrochloric acid (2×400 mL). The layers of 1 mol/L hydrochloric acid were combined. While the combined layer was chilled in an ice water bath, a 30% aqueous NaOH solution was added to make the solution basic (pH 13). The resulting crystals were filtered, washed sequentially with water and diisopropyl ether, and dried under reduced pressure to give (3R,4R)-1-benzyl-N-cyclopropyl-4-methyl-3-pyrrolidinecarboxamide as white crystals (52.2 g).

1. concentrationwas concentrated under reduced pressure
2. additionDiisopropyl ether (800 mL) was added to the residue
3. stirringthe solution was stirred at room temperature for 70 min
4. filtrationThe resulting crystals were filtered
5. dissolutionThe collected crystals were then dissolved in dichloromethane (800 ml)
6. extractionthe solution was extracted with 1 mol/L hydrochloric acid (2×400 mL)
7. temperatureWhile the combined layer was chilled in an ice water bath
8. additiona 30% aqueous NaOH solution was added
9. filtrationThe resulting crystals were filtered
10. washwashed sequentially with water and diisopropyl ether
11. customdried under reduced pressure

ORD record

ord-944f41f53a354f4097ebb780c9d264f8

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106072B2