반응 #2345168

반응 방정식

4-hydroxy-2-adamantyl acetic acid

WSC

Triethylamine

(IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

→

(IS)-3-(4-hydroxy-2-adamantylacetyl)1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

용매

methylene chloride

반응 조건

후처리

1. 1
   기타was gradually changed to room temperature
2. 2
   workup.STIRRINGstirred for 25 hours
3. 3
   세척The reaction mixture was washed with saturated aqueous sodium chloride solution
4. 4
   건조dried by anhydrous sodium sulfate
5. 5
   여과After filtering the drying agent
6. 6
   농축the filtrate was concentrated in vacuo

실험 절차

Triethylamine 0.23 ml was added to a methylene chloride 5 ml solution of (IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.26 g and stirred at O@C for 30 min. 4-hydroxy-2-adamantyl acetic acid 0.26 g and WSC 0.31 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 25 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 (IS)-3-(4-hydroxy-2-adamantylacetyl)1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 25 ml solution of lithium aluminum hydride 70.5 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 methanol=150:1) to obtain the product.

출처