Triethylamine → (IS)-3-(4-methylcyclohexylacetyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

Temperature

0 °C

Triethylamine 0.84 ml was added in a methylene chloride 20 ml solution of (IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.95 g, and stirred at 0° C. for 30 min. 4-methylcyclohexyl acetic acid 0.94 g and WSC 1.35 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 24 hours. The reaction mixture was washed with saturated 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-methylcyclohexylacetyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 30 ml solution of lithium aluminum hydride 0.39 g and refluxed for 1 hour. The reaction mixture was cooled, then added water, and filtered the insoluble material. The filtrate was concentrated in vacuo. The thus obtained residue was purified by means of silica gel column chromatography (Wako gel, C200, chloroform:acetone=10:1) to obtain the product.

1. customwas gradually changed to room temperature
2. stirringstirred for 24 hours
3. washThe reaction mixture was washed with saturated sodium chloride solution
4. dry with materialdried by anhydrous sodium sulfate
5. filtrationAfter filtering the drying agent
6. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-d3c5998ea30a403aa383030583ff9852

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05658923