Hexane → HCID 66977220, compound

Participants

Reaction Steps

A solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (2.0 g, 7.75 mmol) in THF (100.0 mL) was cooled to −78° C. followed by drop wise addition of LDA (1.80 M in THF, 8.80 mL, 15.56 mmol) and the mixture stirred at the same temperature for 45 min followed by addition of dimethyl disulfide (2.21 mL, 23.25 mmol) at −78° C. The temperature of the reaction was slowly raised up to rt and left to stir for 6 h. The reaction was then cooled to 0° C. and quenched by drop wise addition of saturated NH4Cl solution (50 mL), extracted with EtOAc (3×100 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 5% EtOAc:hexane to obtain the product as an orange viscous liquid (1.90 g, 83% yield). MS: 304.19 [M+H]+.

Provenance & Evidence