tert-Butyl acetate → HCID 14986687, compound

Participants

Reaction Steps

To a solution of 0.11 ml cyclohexyl-isopropylamine (0.68 mmol) in 1 ml dry tetrahydrofuran at 0° is added dropwise 0.23 ml (0.57 mmol) of a 2.5M solution of n-butyllithium in hexane. The mixture is allowed to stir for 15 min at 0°. The reaction mixture is then cooled to -78° and 0.077 ml (0.57 mmol) t-butyl acetate is added and the mixture is stirred at -78° for 0.5 h. Then a solution of 0.12 g (0.22 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(tetrahydropyranyloxy)propyl]-1-iodo-hexane in 0.5 ml hexamethylphosphoric triamide is added followed by 1 ml dry tetrahydrofuran. The reaction temperature is raised to -23° and allowed to warm to 0° over a period of 1 h. The reaction is then quenched by the addition of 5 ml saturated aqueous ammonium chloride solution and extracted with ether. The organic layer is washed with water (3×25 ml) and brine, dried, filtered and concentrated to give a yellow oil which is chromatographed using 3:7 ethyl acetate/hexane to yield t-butyl 8-(p-chlorophenylsulfonamido)-4-[3-(tetrahydropyranyloxy)propyl]-octanoate; NMR (CDCl3): delta 2.2 (t,2H), 1.6 (s,9H); IR (neat): 1721 cm-1.

Provenance & Evidence