1,3-Dibromobenzene → (+/-)-trans-6-(3-Bromophenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinol

Participants

Reaction Steps

8.9 ml (12.5 mmol) of a 1.4 M solution of n-butyllithium in hexane were added dropwise, under a nitrogen atmosphere and at -55° C., to a solution of 2.95 g (12.5 mmol) of 1,3-dibromobenzene in 10 ml of dry THF. After 90 min this solution was added via cannula to a solution of 1.2 g (4.17 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone in 10 ml of dry THF and at -20° C. The reaction mixture was allowed to warm up to room temperature overnight, then it was quenched with a saturated NH4Cl solution. The aqueous phase was extracted with AcOEt and the solvent was removed in vacuo. The residue was taken up in Et2O and washed with a 10% HCl solution; the phases were separated and the aqueous phase was brought to pH 14 with a 2N NaOH solution, then extracted with CH2Cl2. The organic phase was dried over Na2SO4, the solvent was removed in vacuo and the crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 94.5:5:0.5 respectively, yielding 0.44 g of the title compound.

Provenance & Evidence