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Lawesson's reagent → 1,1-Dimethylethyl 4-(aminocarbonothioyl)-4-methyl-1-piperidinecarboxylate

HRID 1516482
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1516482
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15](=O)[NH2:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([C:15](=[S:27])[NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 533937931-Boc-4-methylpiperidine-4-carboxamide

Produkt 1

HCID 574733781,1-Dimethylethyl 4-(aminocarbonothioyl)-4-methyl-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 4-carbamoyl-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (2.1 g, 8.7 mmol) in THF (30 mL) was added Lawesson's reagent (3.5 g, 8.7 mmol) at room temperature. The mixture was heated at 50° C. for 3 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was washed with saturated NaHCO3, and brine. After drying (Na2SO4), the solvent was removed in vacuo, and the residue was purified by silica column chromatography with EtOAc/hexanes to afford the desired product.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between EtOAc and H2O
  4. washThe organic layer was washed with saturated NaHCO3, and brine
  5. dry with materialAfter drying (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by silica column chromatography with EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b8e9e93999d24ab3a03132a8217ad1e6
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08227495B2

Notizen zur Reaktion

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