Phthalimide → HCID 18423417, compound

Participants

Reaction Steps

To a solution of 0.344 g (1.26 mmol) of 1-t-butoxycarbonyl-4-(3-hydroxypropyloxymethyl)piperidine (Example 17, Step 3), 0.926 g (6.3 mmol) of phthalimide, and 0.661 g (2.52 mmol) of triphenylphosphine in 10 mL of THF at 0° C. was added dropwise 0.4 mL of diethylazodicarboxylate (DEAD). The reaction mixture was allowed to warm to rt and was stirred for 36 h. To the reaction mixture was added 20 mL of ether and it was filtered through a thin pad of celite. The filtrate was washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 2:1) to give 1-t-butoxycarbonyl-4-(3-phthalimidopropyloxymethyl)piperidine. Removal of the BOC protecting group was achieved as described in Example 4, Step 2 to give the title compound.

Provenance & Evidence