Water → [2-(1-Amino-cyclopropyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 1040444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040444
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([Mg]Br)[CH3:19].O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2([NH2:16])[CH2:19][CH2:18]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 962WaterHCID 232981494-[(tert-Butoxycarbonylamino)methyl]-2-cyanopyridineHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 67390399[2-(1-Amino-cyclopropyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2-cyano-pyridin-4-ylmethyl)-carbamic acid tert-butyl ester (1.2 g, 5.1 mmol) in THF (100 mL) was added ethylmagnesium bromide (3 M, 3.3 mL, 10 mmol) and titanium isopropoxide (2.3 mL, 7.7 mmol). The reaction mixture was stirred at room temperature for 16 h. Water was added (5 mL) and the resulting solids filtered off. The organics were concentrated, then purified by flash chromatography on silica gel using 5-10% MeOH/CH2Cl2 to afford [2-(1-amino-cyclopropyl)-pyridin-4-ylmethyl]-carbamic acid tert-butyl ester as a solid, m/z 264.4 [M+1]+.

Aufarbeitung

  1. filtrationthe resulting solids filtered off
  2. concentrationThe organics were concentrated
  3. custompurified by flash chromatography on silica gel using 5-10% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-1c583627cf7048e5bf7e3b896e4ee8c1
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552205B2

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