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

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To a flask with trifluoromethanesulfonic acid (3.00 mL, 34 mmol) at 0° C. was added dropwise the (S)—N-(4-bromobenzylidene)-1-phenylpropan-2-amine and the reaction was heated to 120° C. and stirred 19 h under N2. The reaction was poured into ice water (20 mL) and basisified with 5 N NaOH (6 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 (410 mg). 1H-NMR shows 92:8 diastereomeric ratio. The residue was purified by ISCO (40 g SiO2, 0-100% EtOAc/hexane) to give the title compound as a light yellow oil.

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