4-Toluenesulfonyl chloride → HCID 53691289, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3,3-bis(4-chlorophenyl)-1-propyloxy) ethanol (3.5 g, 10.8 mmol) in dry THF (25 ml) kept under a nitrogen atmosphere was cooled to 10° C. and a solution of n-butyllithium in hexanes (4.3 ml, 2.5 M) was added dropwise. When addition was complete the reaction mixture was stirred for 1 h at room temperature. p-Toluenesulphonyl chloride (2.1 g, 10.8 mmol) was added and the mixture was stirred at room temperature for 1.5 h. The solvent was evaporated in vacuo and acetone (30 ml) was added to the residue. The mixture was filtered and to the filtrate was added ethyl (R)-3-piperidinecarboxylate (1.8 g, 11.5 mmol) and potassium carbonate (1.5 g, 10.8 mmol). The mixture was heated at reflux temperature for 3 h and then stirred for 2 days at room temperature. The reaction mixture was filtered and the solvent was evaporated in vacuo. Flash chromatography of the residue on silica gel (200 g) using a mixture of n-heptane and ethyl acetate (6:4) as eluent provided 2.0 g (40%) of the title compound as an oil. TLC: rf=0.17 (SiO2 ; n-heptane/ethyl acetate=7.3). 1H NMR (CDCl3)δ 4.13 (t, 1H).

Provenance & Evidence