1,1'-Carbonyldiimidazole → HCID 45087014, compound

trans-1-Benzyl-4-methyl-3-pyrrolidine carboxylic acid (4.04 g) was dissolved in dichloromethane (50 mL). To this solution, 1,1′-carbonyl bis-1H-imidazole (3.58 g) was added and the mixture was stirred at room temperature for 1 hour. While the mixture was chilled in an ice bath, cyclopropylamine (1.53 mL) in dichloromethane (15 mL) was added drop wise and the mixture was stirred at room temperature for 3 hours. Subsequently, the reaction mixture was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from a hexane/diisopropyl ether mixture, and the crystals were filtered, washed with a hexane/diisopropyl ether mixture, and dried under reduced pressure to give trans-1-benzyl-N-cyclopropyl-4-methyl-3-pyrrolidine carboxamide as white crystals (4.07 g).

1. temperatureWhile the mixture was chilled in an ice bath
2. stirringthe mixture was stirred at room temperature for 3 hours
3. washSubsequently, the reaction mixture was washed with water
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was crystallized from a hexane/diisopropyl ether mixture
7. filtrationthe crystals were filtered
8. washwashed with a hexane/diisopropyl ether mixture
9. customdried under reduced pressure

ORD record

ord-0d5cebd688b94847bd8b6f32c350610b

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514451B2