tert-Butyl acetate → HCID 14986687, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.11 mL cyclohexyl-isopropylamine (0.68 mmol) in 1 mL dry tetrahydrofuran at 0° C. is added dropwise 0.23 mL (0.57 mmol) of a 2.5 M solution of n-butyllithium in hexane. The mixture is allowed to stir for 15 minutes at 0° C. The reaction mixture is then cooled to -78° C. and 0.077 mL (0.57 mmol) t-butyl acetate is added and the mixture is stirred at -78° C. for 0.5 hour. Then a solution of 0.12 g (0.22 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(tetrahydropyranyloxy)propyl]-1-iodohexane in 0.5 mL hexamethylphosphoramide is added followed by 1 ml dry tetrahydrofuran. The reaction temperature is raised to -23° C. and allowed to warm to 0° C. over a period of 1 hour. 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