Isobutyronitrile → HCID 89827711, compound

Participants

Reaction Conditions

Reaction Steps

Treat a −78° C. solution of diisopropylamine (35 g, 0.346 mol) in THF (300 mL), under N2, dropwise with a solution of n-butyllithium (2.5 M, 127 mL, 0.317 mol), warm to −30° C. for 0.5 h, re-cool to −78° C. and treat dropwise with a solution of isobutyronitrile (19.9 g, 0.288 mol) in THF (100 mL). Stir the mixture at −78° C. for 0.5 h, treat with a solution of benzyl (2-bromoethyl)carbamate (74 g, 0.288 mol) in THF (100 mL), stir at −78° C. for 1 h, then warm to RT and stir overnight. Treat the mixture with H2O, separate the layers, extract the aqueous layer with EtOAc, wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (15 g, 21% yield). MS (m/z): 247.2 (M+1).

Provenance & Evidence