Sodium Carbonate → HCID 66704854, compound

(3R,4R)-1-Benzyl-N-cyclopropyl-4-methyl-3-pyrrolidinecarboxamide (70.0 g) was dissolved in toluene (700 mL). While this solution was cooled on an ice bath, a borane-dimethyl sulfide complex (90%, 34.3 mL) was added dropwise. The mixture was then stirred for 15 min and was heat-refluxed. After the reaction mixture was cooled to room temperature, a 10% aqueous solution of Na2CO3 (400 mL) was added and the mixture was stirred at 100° C. for 2 hours. The mixture was cooled to room temperature and the toluene layer was separated. The toluene layer was then washed with water (2×250 mL), was dried over anhydrous sodium sulfate, and was concentrated under reduced pressure. The resulting residue was purified by distillation under reduced pressure to obtain (3S,4R)-1-benzyl-3-cyclopropylaminomethyl-4-methylpyrrolidine (62.1 g) as a colorless oil.

1. temperatureWhile this solution was cooled on an ice bath
2. additiona borane-dimethyl sulfide complex (90%, 34.3 mL) was added dropwise
3. temperaturewas heat-refluxed
4. stirringthe mixture was stirred at 100° C. for 2 hours
5. temperatureThe mixture was cooled to room temperature
6. customthe toluene layer was separated
7. washThe toluene layer was then washed with water (2×250 mL)
8. dry with materialwas dried over anhydrous sodium sulfate
9. concentrationwas concentrated under reduced pressure
10. distillationThe resulting residue was purified by distillation under reduced pressure

ORD record

ord-443f33a22c4f4d6590889895c3224acb

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153851B2