Hydrochloric Acid → HCID 67421015, compound

Participants

Reaction Conditions

Reaction Steps

4.0 ml (9.9 mmol, 1.2 eq) of 2.5M n-butyllithium in hexane are added to a solution of 3.59 g (8.26 mmol, 1 eq) of 1,5-bis(benzyloxy)-2-fluoro-4-iodobenzene in 40 ml of tetrahydrofuran, cooled to −70° C. The reaction medium is stirred at −70° C. for 25 minutes and 1.97 g (9.9 mmol, 1.2 eq) of 1-boc-4-piperidone in solution in 20 ml of tetrahydrofuran are added. The reaction medium is stirred at −70° C. for 1 hour and is then left to return to ambient temperature overnight. 30 ml of a saturated solution of ammonium chloride, to which 4 ml of 2M hydrochloric acid have been added, are added to the reaction medium, which is stirred for 20 minutes and is then extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel, elution being carried out with 95/5 heptane/ethyl acetate then 75/25 heptane/ethyl acetate (with 0.1% of TEA).

Provenance & Evidence