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. Author manuscript; available in PMC: 2011 Sep 8.
Published in final edited form as: J Am Chem Soc. 2010 Sep 8;132(35):12216–12217. doi: 10.1021/ja105772z

Scheme 4.

Scheme 4

Synthesis of (S)-(−)-Ropivacaine

i) s-BuLi (1.2 eq), Et2O, TMEDA (4.0 eq), −78 °C, 3 h, then 9, (10 mol%), −45 °C, 3 h, −78 °C, 2,6-dimethylphenyl isocyanate, 2 h, >99:1 er; ii) CF3COOH, CH2Cl2, rt, 10 h, then NaOH; iii) isopropyl alcohol, 1-bromopropane (3.0 equiv), K2CO3 (3.0 equiv), H2O, 100 °C, 6 h.