Sodium Iodide → HCID 10829224, compound

Participants

Reaction Steps

A mixture of 5-bromovaleraldehyde dimethyl acetal (27.5 g, 0.13 mol), Na2CO3 (20.7 g, 0.195 mol), sodium iodide (19.5 g, 0.13 mol) and tert-butyl 1-piperazinecarboxylate (25.5 g, 0.137 mol), in dimethoxyethane (250 ml), was heated at 100° C. for 3 h. Aluminium foil was wrapped around the vessel to exclude light. The mixture was cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure and then EtOAc (50 ml) added and the mixture filtered again to remove inorganic salts. The solvent was removed under vacuum and the residue chromatographed on silica gel eluting with EtOAc to give the title-product (25.7 g, 63%). δ(250 MHz, CDCl3) 1.29-1.71 (6H, m, 3 of CH2); 1.46 (9H, s, OC(Me)3); 2.31-2.39 (6H, m, 3 of CH2); 3.32 (6H, s, CH(OMe)2); 3.41-3.45 (4H, m, 2 of CH2); 4.36 (1H, t, J=6 Hz, CH(OMe)2).

Provenance & Evidence