4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 71775

Reaktionsgleichung

Reaktionsgleichung von HRID 71775
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+].[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>O>[CH2:15]([O:14][C:12]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Produkt 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Piperidine-4-carboxylic acid (64.8 g, 0.5 mol) in H2O (50 mL) was treated with NaOH (44.0 g, 1.1 mol). The reaction mixture was cooled to 0° C. and treated with CbzCl (93.8 g, 0.55 mol). The reaction mixture was stirred at ambient temperature for 4 hours and the mixture was extracted with Et2O (3 150 mL). The aqueous phase was acidified with 6 N HCl (140 mL) and extracted with EtOAc (3 200 mL). The solution was dried over MgSO4, filtered, and concentrated to afford crude piperidine-1,4-dicarboxylic acid monobenzyl ester (120 g), which was used without further purification: MS (ESI) m/z 262 [M−H]+.

Aufarbeitung

  1. extractionthe mixture was extracted with Et2O (3 150 mL)
  2. extractionextracted with EtOAc (3 200 mL)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-faee25c567534f6e93cd002eea407fee
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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