Sodium Iodide → (R)-1-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-hydroxy-propyl)-3-piperidinecarboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of crude (10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2,3-epoxypropane (6.0 g, 20.8 mmol, prepared as described in Example 19), (R)-3-piperidinecarboxylic acid ethyl ester (L)-tartrate (6.24 g, 20.8 mmol), potassium carbonate (11.5 g, 83.2 mmol) and sodium iodide (3.12 g, 20.8 mmol) in dry N,N-dimethylformamide (25 ml) was stirred and heated at 60° C. for 48 h. The reaction mixture was concentrated in vacuo and the residue dissolved in toluene (100 ml) and ethyl acetate (100 ml). The solution was washed with water (2×50 ml), dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a mixture of toluene, ethyl acetate and triethylamine (35:6:1) as eluent to give 4.5 g (53%) of (R)-1-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-2-hydroxy-propyl)-3-piperidinecarboxylic acid ethyl ester as an oil.

Provenance & Evidence