Diisopropylamine → HCID 57425767, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (3.33 g 4.64 ml; 32.92 mmol) in THF (60 ml) at 0° C. was added n-butyllithium (2.5M in hexanes; 13.17 ml; 32.92 mmol). The solution was stirred for 30 minutes then cooled to −78° C. A solution of 3-cyanoazetidine-1-carboxylic acid tert-butyl ester (5 g; 27.43 mmol) in THF (40 ml) was added and the solution stirred for 1 hour. (Bromomethyl)cyclopropane (4.81 g 3.42 ml; 35.67 mmol) was then added dropwise with stirring and the solution stirred for 30 minutes at −78° C., then allowed to warm to ambient temperature, and stirred for 3 hours. The reaction was cooled in an ice bath and quenched with saturated aqueous ammonium chloride. The solvent was evaporated and the residue was partitioned between EtOAc (300 ml) and water (100 ml). The organic phase was separated, dried over MgSO4, filtered and evaporated to give an orange oil. The crude product was passed through a silica gel plug eluted with 15% EtOAc DCM to give the product as a pale yellow oil. (5.25 g)

Provenance & Evidence