Triethylamine → Benzyl 3-[(9Z,12Z)-Octadeca-9,12-Dien-1-Yloxy]-4-(Octyloxy)Pyrrolidine-1-Carboxylate

Participants

Reaction Conditions

Reaction Steps

In 2500 mL RBF, compound 9 (9.7 g, 40.0 mmol) and triethylamine (0.558 ml, 4.0 mmol) were suspended in 100 mL toluene for addition of the sodium hydride (1.76 g, 44 mmol). Heated suspension to 50° C. for 1 h. Cooled back to 23° C. and then added the linoleyl mesylate (13.8 g, 40.0 mmol). Heated slurry up to 80° C. for 18 h. Cooled to 23° C. and poured into 200 mL 1M K2CO3. Extracted with methyl tert-butyl ether (MTBE) and then dried combiend layers over Na2SO4. Filtered, concentrated and purified oil by silica gel chromatogtaphy to obtain monoalkylated product as a slightly yellow oil. In 250 mL RBF, 8 g of the aforementioned oil (16.47 mmol) and triethylamine (0.23 ml, 1.65 mmol) was dissolved in 100 mL toluene for addition of the sodium hydride (0.0.725 g, 18.12 mmol). Heated suspension to 50° C. for 1 h. Cooled back to 23° C. and then added the n-octyl mesylate (3.77 g, 18.12 mmol). Heated slurry up to 80° C. for 21 h or until complete dissappearance of the starting material was observed by HPLC. Cooled to 23° C., diluted with 100 mL hexane and washed with 100 mL 1M K2CO3. Extracted aquoues layer with 100 mL hexane and then washed combined organic layers with 100 mL brine and dried over MgSO4. Filtered and concentrated. Purified by silica gel chromatography to obtain 8.4 g of 10 as a clear oil. Product contains some octyl mesylate but was carried into next reaction.

Provenance & Evidence