Sodium Iodide → trans-tert-Butyl 3-({cyclopropyl[3-[2-(cyclopropyloxy)ethoxy]-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-tert-butyl 3-({cyclopropyl[3-hydroxy-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-1-piperidinecarboxylate (1.0 eq., Example 92) in DMF (0.1 M) was added cesium carbonate (2 eq.), sodium iodide (0.05 eq.) and (2-chloroethoxy)cyclopropane (3 eq.). The reaction mixture was heated at 100° C. for 22 h. After cooling to RT, the reaction was quenched with sat. aq. ammonium chloride and extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 95:5 (v/v) CH2Cl2:MeOH) afforded the title compound as a colorless oil.

Provenance & Evidence