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

HRID 1850796Notes

Reaction equation

[OH:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C@H:11]2[CH2:13][C@H:12]2[CH2:14][CH2:15][OH:16])[CH2:7][CH2:6]1)=[NH:4].[C:17](Cl)(=O)[CH:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.CCOC(C)=O>[CH:18]([C:20]1[O:1][N:2]=[C:3]([N:5]2[CH2:10][CH2:9][CH:8]([C@H:11]3[CH2:13][C@H:12]3[CH2:14][CH2:15][OH:16])[CH2:7][CH2:6]2)[N:4]=1)([CH3:19])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-413a6e42cec94a3dbd24893ce86d6740
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957062B2

Reaction notes

Loading…