Reaktion #79912

Reaktionsgleichung

acetic acid

4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)-benzoic acid ethyl ester

Intermediate 14

4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)-benzoic acid ethyl ester

cyclopropyl amine

sodium cyanoborohydride

→

title compound

Ausbeute 64.5%

4-(5-Cyclopropylamino-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2yl-ethynyl)-benzoic acid ethyl ester

Ausbeute 64.5%

Lösungsmittel

dichloromethane

acetonitrile

water

sodium carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane (×2)
2. 2
   ExtraktionThe combined organic extract
3. 3
   Trocknenwas dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo to an oil

Vorschrift

A solution of 4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)-benzoic acid ethyl ester (Intermediate 14, 0.14 g, 0.4 mmol) in 3 mL of dichloromethane and 2 mL of acetonitrile was treated with cyclopropyl amine(1 mL, 14.45 mmol). After 5 minutes, acetic acid (1 mL) was added followed by sodium cyanoborohydride (0.13 g, 2 mmol). The reaction was stirred overnight at ambient temperature. It was then diluted with water and saturated aqueous sodium carbonate solution and extracted with dichloromethane (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 20% ethyl acetate in hexane as the eluent afforded the title compound (0.1 g, 62%) as a pale yellow solid.

Quelle