Organic Chemistry of Drug Synthesis. Volume 7

aluminum chloride yields the chloroketone ( 42 ). Reaction of that with
pyrrolidine ( 40 ) leads to the alkylation product 43. Catalytic hydrogenation
over palladium reduces the aryl carbonyl group to a methylene probably
via the initially formed labile benzyl alcohol. Thus the anticholinergic
agent 44 is obtained.^4

HO NH

CO 2 H

34

heat NH

HO

35

CH 3 C 6 H 4 SO 2 CH 3

HO NSO^3 C^6 H^4 CH^3 DEAD; Ph 3 PCH 3 C 6 H 5 SO 2 NSO 3 C 6 H 4 CH 3

36

CH 3 C 6 H 4 SO 2 Cl

CN

CN

NSO 3 C 6 H 4 CH 3

39

37

38

NaH

1. HBr


2. H 2 SO 4

CONH 2

NH

40

O

41

Cl COCl

O

42

O

Cl

CONH 2

43

O

O

N

H 2 CONH 2

44

O

N

Protein kinases comprise a series of closely related enzymes that cata-
lyze the phosphorylation of hydroxyl groups in enzymes, which regulate
a wide range of physiological processes. Phosphorylation may either turn
the function of the target on or off. Inhibitors of the protein C kinases
(PKC) that are involved in cell proliferation have attracted particular

HN

N N

O

O O

N(CH 3 ) 2

Ruboxystaurin

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