Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylate → [1-(2,2-Dimethylpropyl)piperidin-4-yl]methanol

HRID 12397

Reaktionsgleichung

Reaktionsgleichung von HRID 12397
[C:1]([N:7]1[CH2:12][CH2:11][CH:10]([C:13](OCC)=[O:14])[CH2:9][CH2:8]1)(=O)[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 1164515Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 21060224[1-(2,2-Dimethylpropyl)piperidin-4-yl]methanolAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

20a (29.5 g, 122 mmol) was dissolved in 200 mL of tetrahydrofuran and cooled to 0° C. Lithium aluminum hydride (s) (10.6 g, 279 mmol) was added slowly and the reaction was allowed to warm to rt and stirred for 24 h. The reaction was quenched by slow addition of sodium sulfate hydrated crystals (Na2SO4.10H2O) until there was no bubbling on addition followed by 20 mL of water. The mixture was filtered through Celite®, and the Celite® washed with diethyl ether. The solvent was removed from the filtrate to provide 20 g (97%) of the desired product as a white solid. 1H NMR (400 MHz, CDCl3).

Aufarbeitung

  1. temperatureto warm to rt
  2. customThe reaction was quenched by slow addition of sodium sulfate hydrated crystals (Na2SO4.10H2O) until there
  3. additionbubbling on addition
  4. filtrationThe mixture was filtered through Celite®
  5. washthe Celite® washed with diethyl ether
  6. customThe solvent was removed from the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-cc3d8336b3cb4a12933dd1ca2bc5b351
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728008B2

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