Sodium t-butoxide → HCID 58478442, compound

Participants

Reaction Steps

4-[3-(4-Bromo-2-methyl-phenylamino)-propyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (3.78 g, 7.81 mmol, 1 eq) was dissolved in THF (80 mL). A 1M solution of NaOt-Bu in THF (7.8 mL, 7.8 mmol, 1 eq) was added and the reaction mixture was stirred for 2 h at rt. The reaction mixture was stirred for 48 h, quenched with 250 mL of water, transferred to a separatory funnel and extracted with dichloromethane (2×150 mL). The combined organics were dried over Na2SO4 and purified by column chromatography on silica gel (200 g column, 50% EtOAc in heptanes; 50 mL/min). This gave 2.49 g (73%) of the title compound as a beige gum.

Provenance & Evidence