Me MeO. OMe MeO OMe Verapamil (гасemic) Me CN MeO. OMe H. MeO OMe (A) (racemic) (B) Ме MeO HN OMe Br Br MeO OMe Isopropyl 3,4-Dimethoxyphenylacetonitrile bromide 1-Bromo-3-chloropropane H,N. OMe + Cl-C-OEt ОМе (D) Ethyl chloroformate
Verapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise.
Q. How do you account for the regioselectivity of the nucleophilic displacement
involved in converting (C) to (B)?
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