Ammonium Chloride → acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of mesyl chloride (0.1 ml) in 1 ml of dry THF is added dropwise under argon over a period of 15 minutes to a cooled (−20° C.) solution of 4-(6-acryloyloxyhexyloxy)benzoic acid (0.38 g) and triethylamine (0.52 ml) in 10 ml of dry THF. The obtained reaction mixture is stirred for 60 min at −20° C. then treated with a solution of (S)-dinaphthalen-2-ylpyrrolidin-2-ylmethanol (0.46 g) in 5 ml of dry THF and further stirred at −20° C. for 2 h. The reaction mixture is then allowed to warm to room temperature, and stirring is continued overnight. The reaction mixture is then poured into 40 ml of saturated NH4Cl solution and extracted with 4×40 ml of diethyl ether and 20 ml of dichloromethane. The combined organic extracts are washed with saturated NaCl solution (2×80 ml), dried over MgSO4, filtered and evaporated to give a brownish residue. This was purified by chromatography over a short silica column (CH2Cl2 / Et2O : 19 / 1 ) to give acrylic acid (S)-6-[4-[2-(hydroxydinaphthalen-2-ylmethyl)pyrrolidine-1-carbonyl]phenoxy]hexyl ester as a white crystalline material. Yield 0.51 g.

Provenance & Evidence