tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 66864309, Verbindung

HRID 2093094

Reaktionsgleichung

Reaktionsgleichung von HRID 2093094
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N-:18]C(C)C)(C)C.[Li+].[C:23]([O:28][CH2:29][CH2:30]Br)(=[O:27])[C:24]([CH3:26])=O>C1COCC1>[NH:18]1[C:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][C:10]=2[CH:26]=[C:24]1[C:23]([O:28][CH2:29][CH3:30])=[O:27]

Komponenten

5

Edukt 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 86587973Bromoethyl pyruvate

Produkt 1

HCID 66864309HCID 66864309, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of N-boc-4-piperidone (1 eq.) and lithium di-isopropyl amide (1 eq.) in THF was stirred at −78° C. and for 2 hrs. A bromoethyl pyruvate (1.2 eq.) was added to above reaction mixture and stirred for 30 min. Reaction mixture was then quenched with ammonia solution and then extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness. The residue was then dissolved in dichoromethane and was added silica (100-200 mesh), stirred for overnight at room temperature. Crude was then purified by silica gel column chromatography to yield 5-tert-butyl 2-ethyl 1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxylate.

Aufarbeitung

  1. customReaction mixture
  2. customwas then quenched with ammonia solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was then dissolved in dichoromethane
  7. additionwas added silica (100-200 mesh)
  8. stirringstirred for overnight at room temperature
  9. customCrude was then purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6f708db8a9684e74b0489fe18c279fe5
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440830B2

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