Sodium hydride → 4-(1-Tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 1433085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433085
[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([CH2:33]Br)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:33][CH:30]2[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:26])[CH2:28][CH2:29]2)[C:15](=[O:19])[CH2:14]1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60%, 0.27 g, 6.7 mmol) is added to a solution of 4-benzyloxycarbonyl-2-oxo-piperazine (1.58 g, 6.7 mmol) in dry DMF (40 mL). After 30 minutes 4-bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.87 g, 6.7 mmol) is added and the reaction is allowed to stir for 16 h. The solvent is removed in vacuo and the residue is dissolved in ether and washed with NH4Cl. The aqueous phase is back-extracted with ether and the combined ether fractions are washed with water and brine to provide 4-(1-tert-butoxycarbonyl-piperidin-4-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester which is used without further purification. 1H NMR (300 MHz, CDCl3) δ 7.36 (s, 5H), 5.16 (d, 2H), 4.16 (s, 2H), 4.13 (br, 2H), 3.73-3.69 (m, 2H), 3.44-3.30 (m, 6H), 2.68 (bt, 2H), 1.85-1.73 (m, 1H), 1.58 (bd, 2H), 1.46 (s, 9H), 1.25-1.10 (m, 2H); MS (ion spray) 432 (M+H)+.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in ether
  3. washwashed with NH4Cl
  4. extractionThe aqueous phase is back-extracted with ether
  5. washthe combined ether fractions are washed with water and brine

Quellen und Nachweise

ORD-Eintrag
ord-ee2daafae3ac4425910a0682e8fd7579
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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