Methyl iodide → 6-Methoxy-10-(4-methoxy-phenyl)-7-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

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Reaction Steps

At −78° C., combine 7-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (chiral) (0.027 g, 0.067 mmol), and CH3Li (0.09 ml, 1.6M), then add t-BuLi (0.1 ml, 1.7M). After 30 minutes add CH3I (0.04 ml, 0.61 mmol) and remove cooling. After 1 hour at r.t., add ammonium chloride solution solution and ethyl acetate. Wash organic layer with water, dry over anhydrous sodium sulfate, remove solvent in vacuo to yield the titled compound (0.026 g, 100%). 1H NMR (CDCl3):): 7.27 (d, J=8.8 Hz, 2H), 6.99 (s, 1H), 6.93 (d, J=8.8 HZ, 2H), 6.89 (s, 1H), 3.87 (s, 3H), 3.86 (s, 3H), 3.2 (m, 2H), 2.85 (dd, J=4 and 11, 1H), 2.48 (d, J=14 Hz, 1H), 2.06 (m, 1H), 1.8-0.8 (m, 8H).

Provenance & Evidence