Sodium Hydroxide → (1R,3S)-1-(4-iodophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Conditions

Reaction Steps

To a flask with the crude N-(4-iodobenzylidene)-1-phenylpropan-2-amine (1.17 g) was added trifluoromethanesulfonic acid (6.00 mL, 67805 μmol) and the reaction was heated to 120° C. and stirred 5 h under N2. The reaction was cooled to RT, poured into ice water (20 mL), and basisified with 5 N NaOH (15 mL). The aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with saturated NaCl (20 mL), dried (MgSO4), and concentrated to give a yellow/brown oil. The residue was purified by ISCO (40 g SiO2, 0-100% EtOAc/hexane) to give (1R,3S)-1-(4-iodophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline as a brown oil.

Provenance & Evidence