Cyclopentanone → HCID 58718602, compound

Cyclopentanone (12.7 ml, 143 mmol) was added to tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate (26.6 g, 143 mmol) in a mixture methanol:toluene 3:1 (600 ml:200 ml) and the reaction mixture was stirred at room temperature for 1.5 hours under nitrogen. The mixture was then evaporated to 50 ml, azeotroped three times with methanol:toluene 3:1 (600 ml:200 ml) and concentrated in vacuo. The reaction mixture was taken up in methanol (250 ml), cooled down to 0° C. and sodium borohydride (7.5 g, 200.2 mmol) was added portionwise. After completion of the reaction, water (50 ml) was added and the solvent was evaporated. The residue was diluted with more water (150 ml) and extracted three times with dichloromethane (250 ml). The organic phases were combined, dried over magnesium sulfate, and concentrated in vacuo to provide the title compound as a gum, 36.1 g (99.4%).

1. customThe mixture was then evaporated to 50 ml
2. customazeotroped three times with methanol:toluene 3:1 (600 ml:200 ml)
3. concentrationconcentrated in vacuo
4. temperaturecooled down to 0° C.
5. additionwas added
6. customthe solvent was evaporated
7. additionThe residue was diluted with more water (150 ml)
8. extractionextracted three times with dichloromethane (250 ml)
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated in vacuo

ORD record

ord-67f1378bedfd4f0ebbe08d249ed3387a

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122683B2