(4aS,8aR)-4a-(3-Methoxyphenyl)-2-methyloctahydroisoquinolin-6(2H)-one → Ammonium Hydroxide

Participants

Reaction Steps

To a solution of 1.1 g (0.04 mol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro4a-(3-methoxyphenyl)-2-methyl-6-isoquinolinone in 50 ml of Et2O and 50 ml of dry THF, under a nitrogen atmosphere and at 0° C., 10.3 ml (0.02 mol) of a 2.0 M solution of phenyllithium in benzene were added dropwise. 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, then the combined organic phases were washed with a saturated NaCl solution and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 86:10:0.6 respectively, yielding 0.65 g of the title compound.

Provenance & Evidence