Diisopropylamine → HCID 18975666, compound

Participants

Reaction Conditions

Reaction Steps

A solution of butyllithium in hexane (2.5M; 80 ml) was added to a solution of diisopropylamine (27.8 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (28.6 ml) in tetrahydrofuran (188 ml) stirring at 0° C. Stirring was continued for 0.5 hours then the mixture was cooled to -78° C. and cyclopropanecarbonitrile (13.4 g) was added. After stirring at -78° C. for a further 1 hour cyclopentylmethylbromide (37.6 g) was added slowly, then the mixture allowed to warm to ambient temperature and stirred for a further 18 hours. The mixture was poured onto water (11) then extracted with ethyl acetate (4×150 ml). The combined extracts were washed with brine then dried over magnesium sulphate and then the solvent was removed in vacuo. Solid material was removed by filtration and the residual oil triturated with ether, solid material again being removed by filtration. The residual oil was then purified by distillation under reduced pressure giving 1-(cyclopentylmethyl)cyclo-propanecarbonitrile (8.9 g) as an oil, bp 50° C./1 mbar.

Provenance & Evidence