Triethylamine → HCID 67723149, compound

Participants

Reaction Steps

Triethylamine 14.0 gl was added to a methylene chloride 1 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 15.9 mg and stirred at O@C for 30 min. 5-phenyl-2-adamantyl acetic acid 22.6 mg and WSC 19.3 mg were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 64 hours. The reaction mixture was washed with saturated aqueous sodium chloride solution and dried by anhydrous sodium sulfate. After filtering the drying agent, the filtrate was concentrated in vacuo to obtain crude (1S)-3-(5-phenyl-2-adamantylacetyl)1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 3 ml solution of lithium aluminum hydride 3.8 mg and refluxed under heating for 1.5 hours. The reaction mixture was cooled, then water was added thereto and the insoluble material was removed by filtration. The filtrate was concentrated in vacuo. The thus obtained residue was purified by means of silica gel column chromatography (Wako gel, C200, chloroform: acetone 20:1) to obtain the product. Yield: 7.0 mg (Yield 21%)

Provenance & Evidence