Bromobenzene → (+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyI-4a-(3-methoxyphenyl)-6-phenyl-6-isoquinolinol

Participants

Reaction Conditions

Reaction Steps

30 ml (41.7 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 6.5 g (41.7 mmol) of bromobenzene in 30 ml of dry THF. After 1 h the solution was allowed to warm up to -20° C. and a solution of 2.4 g (8.3 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone in 20 ml of dry THF was added. The reaction mixture was allowed to warm up to room temperature overnight, then it was quenched with 30 ml of a 5% HCl solution and the phases were separated. The aqueous phase was extracted with AcOEt, then brought to pH 14 with a 2N NaOH solution and extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 0.79 g of the title compound.

Provenance & Evidence