Diethyl Malonate → Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonate

HRID 550788

Reaktionsgleichung

Reaktionsgleichung von HRID 550788
C1(S(O[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)(=O)=O)C=CC=CC=1.[C:24]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].CC[O-].[Na+].CCO>CCO>[CH2:29]([O:28][C:26](=[O:27])[CH:25]([CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:16]1)[C:24]([O:32][CH2:33][CH3:34])=[O:31])[CH3:30]

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 23706232Ethanol sodium ethoxideHCID 866191351-Tert-butoxycarbonylpiperidin-4-yl benzenesulfonate

Produkt 1

HCID 59605280Diethyl 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-tert-butoxycarbonylpiperidin-4-ol, triethylamine, benzenesulfonyl chloride, and methylene chloride was stirred at ambient temperature for 2 days to yield 1-tert-butoxycarbonylpiperidin-4-yl benzenesulfonate. A mixture of 1-tert-butoxycarbonylpiperidin-4-yl benzenesulfonate obtained, diethyl malonate, 20% NaOEt-EtOH, and EtOH was heated under reflux with stirring for 22 hours to yield diethyl[1-(tert-butoxycarbonyl)piperidin-4-yl]malonate. A mixture of diethyl [1-(tert-butoxycarbonyl)piperidin-4-yl]malonate obtained, lithium borohydride, toluene, and THF was stirred at 60° C. for 18 hours to yield 2-(1-tert-butoxycarbonylpiperidin-4-yl)propane-1,3-diol, which was stirred together with 4M HCl-dioxane solution in MeOH at ambient temperature for 1 hour to yield 2-piperidin-4-ylpropane-1,3-diol hydrochloride.

Aufarbeitung

  1. customobtained
  2. temperatureunder reflux

Quellen und Nachweise

ORD-Eintrag
ord-2ea39f6b43514390b30e9904b0204f6a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947690B2

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