Lipoic acid → 3-[(3R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propyl 5-[(3R)-1,2-dithiolan-3-yl]pentanoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid 6 (500 mg, 2.42 mmol) in DMF (5 mL) was added K2CO3 (1.4 g, 9.69 mmol) at room temperature and the mixture was stirred for 30 min. Then a solution of hydrochloride salt of (2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triol 5 (581 mg, 2.1 mmol) in DMF (5 mL) was added to the reaction mixture and the mixture was heated at 60° C. for 16 h. The reaction mixture was then filtered through a celite pad, washed with DCM (100 mL). The filtrate was concentrate under reduced pressure to get crude which was purified by column chromatography using 100-200 mesh silica gel and eluting with 6% methanol in DCM to afford 3-[(3R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propyl 5-[(3R)-1,2-dithiolan-3-yl]pentanoate, compound 7 (300 mg, 30%) as brown oil.

Provenance & Evidence