Potassium Carbonate → HCID 10906240, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the above alcohol (0.60 g, 2.0 mmol) in dry THF (15 ml) was placed under an atmosphere of nitrogen and then cooled on an ice-bath. A solution of n-butyllithium in hexanes (0.88 ml, 2.5 M) was added dropwise at 10° C. When addition was complete the mixture was stirred at 10° C. for 30 minutes. Methanesulfonyl chloride (0.25 g, 2.2 mmol) was added and the reaction mixture was stirred at room temperature for 90 minutes. The volatiles were evaporated in vacuo leaving a residue which was dissolved in acetone (20 ml). Ethyl (R)-3-piperidinecarboxylate (0.50 g, 3.0 mmol) and potassium carbonate (0.7 g, 5 mmol) were added and the suspension was stirred at room temperature for 16 h and the heated at reflux temperature for 7 h. The cooled reaction mixture was filtered and the solvent was evaporated in vacuo. The oily residue was submitted to column chromatography on silica gel (150 g) using a mixture of ethyl acetate and n-heptane (2:3) as eluent. Collecting the proper fractions afforded 0.4 g of (R)-N-(2((3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Provenance & Evidence