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 chilled in an ice water bath, a borane/dimethyl sulfate complex (90%, 34.3 mL) was added dropwise. The mixture was then stirred for 15 min, was refluxed and was allowed to cool to room temperature. A 10% aqueous Na2CO3 solution (400 mL) was added, and the mixture was stirred at 100° C. for 2 hours and was then allowed to cool to room temperature. The toluene layer was separated, washed with water (2×250 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by distillation under reduced pressure to give (3S,4R)-1-benzyl-3-cyclopropylaminomethyl-4-methylpyrrolidine as a colorless oil (62.1 g).

1. temperatureWhile this solution was chilled in an ice water bath
2. additiona borane/dimethyl sulfate complex (90%, 34.3 mL) was added dropwise
3. temperaturewas refluxed
4. stirringthe mixture was stirred at 100° C. for 2 hours
5. temperatureto cool to room temperature
6. customThe toluene layer was separated
7. washwashed with water (2×250 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. distillationThe resulting residue was purified by distillation under reduced pressure

ORD record

ord-5c946a1d7f1a4c748f7959e3df865627

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514451B2