Potassium Carbonate → 2-((1S,2R)-2-(1-(5-isopropyl-1,2,4-oxadiazol-3-yl)piperidin-4-yl)cyclopropyl)ethanol

Temperature

80 °C

N-hydroxy-4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboximidamide (4.8 g, 21.10 mmol) was dissolved in Pyridine (60 ml) and isobutyryl chloride (18.44 ml, 176 mmol) was added. The mixture was stirred at 80° C. for 3 h and the solvent was evaporated to dryness. The residue was dissolved in MeOH (100 ml) and potassium carbonate (24.32 g, 176 mmol) was added. The mixture was stirred at 50° C. for 2 h. Another potassium carbonate (24.32 g, 176 mmol) was added and the mixture was stirred at 50° C. for another 2 h. The mixture was cooled down and diluted with EtOAc (100 mL), washed with water, sat. NH4Cl, dried over MgSO4, evaporated. The crude material was purified by silica gel column eluting with 20-70% EtOAc in hexane to afford the desired product. LC/MS (m/z): 280 (M+H)+.

1. customthe solvent was evaporated to dryness
2. dissolutionThe residue was dissolved in MeOH (100 ml)
3. stirringThe mixture was stirred at 50° C. for 2 h
4. stirringthe mixture was stirred at 50° C. for another 2 h
5. temperatureThe mixture was cooled down
6. washwashed with water, sat. NH4Cl
7. dry with materialdried over MgSO4
8. customevaporated
9. customThe crude material was purified by silica gel column
10. washeluting with 20-70% EtOAc in hexane

ORD record

ord-413a6e42cec94a3dbd24893ce86d6740

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957062B2