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. Author manuscript; available in PMC: 2010 Jan 8.
Published in final edited form as: J Med Chem. 2009 Jan 8;52(1):62–73. doi: 10.1021/jm800817h

Scheme 1.

Scheme 1

Synthesis of the Target Reboxetine Analogs 1, 2, 3, and 4a

aReagents and conditions: (a) NaH, DMF, rt, 2 h; I2, THF, 0 °C to rt, 30 min. (b) TFA, CH2Cl2, 0 °C to rt, 2 h. (c) Cr(CO)6, n-Bu2O, THF, reflux, 60 h. (d) DIAD, PPh3, THF, 0 °C to rt, 48 h. (e) CBr4, PPh3, CH2Cl2, 0 °C to rt, 30 min. (f) 2-methylbenzenethiol, Cs2CO3, DMF, 95 °C, 18 h.