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. Two steps are required to convert (D) to (C). The first is treatment of (D) with ethyl chloroformate. What is the product of this first step? What reagent can be used to convert this product to (C)?

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