Ethyl bromopyruvate → 2-Piperidine-4-yl-thiazole-4-carboxylic acid ethyl ester

HRID 507288

Reaktionsgleichung

Reaktionsgleichung von HRID 507288
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20]([C:19]1[N:15]=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[S:16][CH:18]=1)=[O:21])[CH3:24]

Komponenten

4

Edukt 2

HCID 66144Ethyl bromopyruvateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

Produkt 1

HCID 579359592-Piperidine-4-yl-thiazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 10 g (41 mmol) 4-thiocarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (commercially available) and 7.98 g (41 mmol) ethyl bromopyruvate (commercially available) in 120 ml ethanol was stirred at 70° C. for 90 min. The mixture was evaporated to dryness, Na2CO3 aq. was added and the residue was extracted with ethyl acetate. The organic phases were washed with NaCl aq., dried with MgSO4 and evaporated to dryness. The residue was purified on silica eluting with DCM/MeOH/25% NH3 in water 100/20/1 to yield after evaporation of the product fractions 7.28 g (74%) of the title compound as light brown solid.

Aufarbeitung

  1. customThe mixture was evaporated to dryness, Na2CO3 aq.
  2. additionwas added
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic phases were washed with NaCl aq.
  5. dry with materialdried with MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified on silica eluting with DCM/MeOH/25% NH3 in water 100/20/1
  8. customto yield
  9. customafter evaporation of the product fractions 7.28 g (74%) of the title compound as light brown solid

Quellen und Nachweise

ORD-Eintrag
ord-0d3c725b12274cf9a1c6d1826071b2fb
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786143B2

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