4-(1-Tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester → 4-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1433086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433086
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13](=[O:31])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([CH2:17][N:14]2[CH2:15][CH2:16][NH:11][CH2:12][C:13]2=[O:31])[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Komponenten

4

Edukt 1

HCID 234473564-(1-Tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester

Produkt 1

HCID 234475144-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-(1-tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (2.3 g, 5.4 mmol) in methanol (75 mL) is purged with nitrogen and 10% Pd on carbon (0.3 g) is added, and the reaction is again purged with nitrogen. The reaction is placed on a Parr shaker under hydrogen for 16 h. After the system is purged of hydrogen, the catalyst is filtered and washed with methanol. The filtrate is concentrated to provide 4-(2-oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester which is used without further purification. MS (EI) 298 (M+H)+.

Aufarbeitung

  1. additionis added
  2. customthe reaction is again purged with nitrogen
  3. customAfter the system is purged of hydrogen
  4. filtrationthe catalyst is filtered
  5. washwashed with methanol
  6. concentrationThe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-da9b6cced0694fb6878e72b9f3d67083
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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