tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate → 4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 242562

Reaktionsgleichung

Reaktionsgleichung von HRID 242562
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)([OH:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylateHCID 178478191HCID 178478191, Verbindung

Produkt 1

HCID 593412124-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-cooled solution 3,3-Dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.6 g, 7.2 mmol) in THF (20 mL) was added 4-chlorophenylmagnesium bromide (1 M in ether, 15 mL, 15 mmol). The solution was allowed to warm to about room temperature, then stirred at room temperature for about 22 hours. The reaction was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, then purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate) to yield the title compound as a colorless oil.

Aufarbeitung

  1. temperatureto warm to about room temperature
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. custompurified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-78bdd389d3534e50b6c0cd096fb8ef8e
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653096B2

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