Reaktion #74412

Reaktionsgleichung

Water

2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-(piperidin-4-ylmethyl)thiazol-4(5H)-one

methanesulfonyl chloride

triethylamine

→

title compound

Ausbeute 42.5%

2-((2S)-Bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-((1-(methylsulfonyl)piperidin-4-yl)methyl)thiazol-4(5H)-one

Ausbeute 42.5%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe crude product was extracted with CH2Cl2 (3×60 mL)
2. 2
   WaschenThe combined organic extracts were washed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To a solution of 2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-(piperidin-4-ylmethyl)thiazol-4(5H)-one (64 mg, 0.20 mmol) in CH2Cl2 (1.5 mL) was added methanesulfonyl chloride (Aldrich, 34 mg, 0.30 mmol) and triethylamine (60 mg, 0.60 mmol), and the reaction mixture was stirred at room temperature for ca. 18 h. Water (30 mL) was then added, and the crude product was extracted with CH2Cl2 (3×60 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography (silica gel, 0-3% MeOH in CH2Cl2) afforded the title compound as a white solid (34 mg). MS (ESI, pos. ion) m/z: 400 (M+H).

Quelle