4-Toluenesulfonyl chloride → HCID 11070095, compound

Participants

Reaction Steps

A solution of the above alcohol (4.2 g, 14.3 mmol) in dry THF (30 ml) was placed under an atmosphere of nitrogen and placed on an ice-bath. A solution of n-butyllithium in hexanes (5.7 ml, 2.5 M) was added dropwise within 15 minutes and the mixture was stirred for another 15 minutes. p-Toluenesulfonyl chloride (2.7 g, 14.0 mmol) was added in one portion and the mixture was stirred at room temperature for 30 minutes. The solvent was evaporated in vacuo keeping a low bath temperature. The oily residue was dissolved in acetone (25 ml) and ethyl (R)-3-piperidinecarboxylate (3.3 g, 21.0 mmol) and potassium carbonate (3.5 g, 25.0 mmol) were added. The mixture was stirred at room temperature for 120 h. The mixture was filtered and the solvent was evaporated in vacuo. The oily residue was submitted to column chromatography on silica gel (100 g) using a mixture of ethyl acetate and n-heptane (2:3) as eluent. Collecting the proper fractions afforded 3.0 g of (R)-N-(3-(2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)ethoxy)-1-propyl)-3-piperidinecarboxylic acid ethyl ester as an oil. TLC: rf=0.19 (SIC2 ; ethyl acetate/n-heptane=1:1).

Provenance & Evidence