N'-Hydroxy-2-methylpropanimidamide → 1-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

HRID 1467993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467993
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[OH:10]/[N:11]=[C:12](/N)\[CH:13]([CH3:15])[CH3:14]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH:13]([C:12]1[N:9]=[C:8]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[O:10][N:11]=1)([CH3:15])[CH3:14]

Komponenten

5

Edukt 2

HCID 5712089N'-Hydroxy-2-methylpropanimidamideHCID 218978254-Hydroxypiperidine-1-carbonitrile

Produkt 1

HCID 218977441-(3-Isopropyl-1,2,4-oxadiazol-5-YL)piperidin-4-OL

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-hydroxypiperidine-1-carbonitrile (0.4 g, 3.1 mmol) in THF (10 mL), (E)-N′-hydroxyisobutyrimidamide (0.35 g, 35 mmol) and ZnCl2 (1M solution in THF) (4.7 mL) were added and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuo and the resulting crude was dissolved in 4N HCl in ethanol-water (1:1) and stirred at 60-70° C. for 2-3 h. The reaction was quenched by saturated NaHCO3 and the organic layer was separated and concentrated. The residue on column chromatography gave the title compound. (0.280 g, 41.8%)

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting crude was dissolved in 4N HCl in ethanol-water (1:1)
  3. stirringstirred at 60-70° C. for 2-3 h
  4. customThe reaction was quenched by saturated NaHCO3
  5. customthe organic layer was separated
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89143c5012fb4e74b989f2a9b77c262d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000175B2

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