Sodium hydride → 4-(3-Methoxycarbonyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 80635

Reaktionsgleichung

Reaktionsgleichung von HRID 80635
[CH2:1]([O:3][C:4]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)=[O:5])C.[H-].[Na+].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23](OS(C)(=O)=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:8]2[CH:9]=[N:10][C:6]([C:4]([O:3][CH3:1])=[O:5])=[N:7]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178418794HCID 178418794, Verbindung

Produkt 1

HCID 577084074-(3-Methoxycarbonyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1H-[1,2,4]triazole-3-carboxylic acid ethyl ester (1.05 g, 8.23 mmol) in dimethylformamide (50 mL) was added sodium hydride (60%, 0.395 g, 9.88 mmol). The solution was stirred at room temperature for 20 minutes followed by 1 hour at 70° C. 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (2.3 g, 8.23 mmol) was then added in a single portion and heated at 70° C. for 40 hours. The solution was cooled to 0° C. and the salt precipitate was removed by filtration. The filtrate was diluted with dichloromethane and washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatograph on silica gel with Hexanes and EtOAc to afford the desired product. 1H NMR (CDCl3): δ 8.18 (1H, s), 4.40 (1H, m), 4.22 (2H, m), 3.96 (3H, s), 2.82 (2H, m), 2.12 (2H, m), 1.94 (2H, m), 1.41 (9H, s).

Aufarbeitung

  1. waitfollowed by 1 hour at 70° C
  2. temperatureheated at 70° C. for 40 hours
  3. temperatureThe solution was cooled to 0° C.
  4. customthe salt precipitate was removed by filtration
  5. additionThe filtrate was diluted with dichloromethane
  6. washwashed with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatograph on silica gel with Hexanes and EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c6ee8b84d5e34e3ea897045e3e8729c8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846675B2

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