Hydrochloric Acid → HCID 20377405, compound

Participants

Reaction Steps

To a stirred solution of 85 ml of 0.98 M diborane in tetrahydrofuran, maintained at about 10° C. under a nitrogen atomosphere, add a solution of 8.16 g 1-octadecanoyl-3-hydroxyazetidine in 420 ml dry tetrahydrofuran over a period of 1.5 hours. Stir for one hour at room temperature then heat for 1.5 hours at 55°-60° C. Allow the reaction mixture to cool to room temperature and cautiously acidify with 30 ml 6 M aqueous hydrochloric acid. Reflux for one hour and distill in vacuo until about 150 ml solvent is removed. Dilute the residue with 450 ml water and basify with 20 ml 50% aqueous sodium hydroxide. Extract three times with 150 ml portions of ethyl ether, dry the combined ethereal extracts over anhydrous sodium sulfate, and strip off solvent in vacuo. Dissolve the residue in 150 ml ethanol containing 12 ml 1.9 M ethereal hydrochloric acid and reflux under nitrogen for 0.5 hour. Remove the solvent in vacuo and triturate the residue with 280 ml ethyl ether to obtain 1-octadecyl-3-hydroxyazetidine hydrochloride, m.p. 108.5°-115° C. Stir this hydrochloride salt with 120 ml water, 10 ml 2.5 M sodium hydroxide and 40 ml methylene chloride for one hour. Separate the layers and extract the aqueous layer three times with 100 ml portions of methylene chloride. Combine the organic layer and extracts, dry over anhydrous sodium sulfate and remove the solvents in vacuo to obtain 1-octadecyl-3-hydroxyazetidine, m.p. 75.5°-78° C.

Provenance & Evidence