Methyl iodide → 2-(2-Methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131399
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@@H:11]1[CH2:23][CH2:24][OH:25])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:26]I>O1CCCC1.[Cl-].[NH4+]>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]1[CH2:23][CH2:24][O:25][CH3:26])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69212205(S)-di-tert-Butyl 2-(2-hydroxyethyl)piperazine-1,4-dicarboxylate

Produkt 1

HCID 692102832-(2-Methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Add sodium hydride (0.675 g, 16.9 mmol) in portions to a 0° C. solution of (S)-2-(2-hydroxyethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester (3.72 g, 11.3 mmol) in tetrahydrofuran (50 mL) and stir. After 20 minutes, add methyl iodide (1.4 mL, 22.5 mmol) dropwise. Allow the mixture to reach room temperature overnight, dilute with saturated ammonium chloride and extract three times with ethyl acetate. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure. Purify by flash chromatography, eluting with a step gradient starting with dichloromethane up to 7% 2N ammonia-methanol in dichloromethane to obtain 2-(2-methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester.

Aufarbeitung

  1. waitAllow the mixture to reach room temperature overnight
  2. extractionextract three times with ethyl acetate
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate under reduced pressure
  5. customPurify by flash chromatography
  6. washeluting with a step gradient

Quellen und Nachweise

ORD-Eintrag
ord-c34f260e1d414b6393a191aa6b549165
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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