Benzoyl chloride → HCID 131732043, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,5-bis(bromomagnesium)pentane (1.0 eq.) in THF (0.05 M) at −78° C. was added a solution of CuCN-2LiCl prepared from CuCN (1.0 eq.) and LiCl (2.0 eq.) in THF (0.9 M with respect to CuCN). The resulting mixture was stirred at −78° C. for 30 min. A solution of trans-tert-butyl 3-{[(3-bromo-5-iodobenzyl)(cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-1-piperidinecarboxylate (1.0 eq.) from the previous step in THF (0.2 M) was then added and the reaction mixture was warmed to RT over 1 h. Finally, benzoyl chloride (1.5 eq.) was added and the reaction mixture was stirred for another hour. The reaction mixture was quenched with the addition of water and subsequently extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 2:98 (v/v)→15:85 (v/v) MeOH:CH2Cl2) afforded the title compound as a brown oil.

Provenance & Evidence