O

Clomifene acts by enhancing follicular growth caused by ovulation. The primary indication for using clomifene is induction of ovulation in non-ovulating women who still have some estrogen production. Clomifene is used for infertility in order to increase reproductive properties of oligoovulatory women who have three or four ovulatory cycles per year, leading to normal monthly ovulation. Synonyms of this drug are clomid, serophene, clostibegit, and others.

Tamoxifen: Tamoxifen, (Z)-2-[p-(1,2-diphenyl-1-butenyl)phenoxy]N,N-dimethylethy-lamine (28.2.8), is synthesized from a-ethyldezoxybenzoin. Interaction of this with 4-methoxyphenylmagnesium bromide gives the corresponding carbinol (28.2.5). Its dehydration in acidic conditions gives a derivative of stilbene (28.2.6), and further heating of which with quinidine hydrochloride as a demethylating agent gives 2-[p-(1,2-diphenyl-1-butenyl)phenol] (28.2.7). The phenolic hydroxyl is further alkylated by dimethy-laminoethylchoride using sodium ethoxide as a base, which forms a mixture of E and Z isomers of the final product. The desired Z isomer, tamoxifen (28.2.8) is isolated by fractional crystallization from petroleum ester.

OCH3 28.2.5

h5c2\

H5C2\ h5C2/

N-CH2-CH2-Cl H5C2/

An alternative way of making tamoxifen is the direct interaction in the Grignard reaction of the a-ethyldeoxybenzoin and the 4-(2-dimethylaminoethoxy)phenylmagnesium bromide, and further dehydration of the resulting carbinol (28.2.9) followed by subsequent separation of the mixture of E and Z isomers [49-56].

C2H5

H5C2V

H5C2

h5c2

c2h5

N-CH2-CH2-O

h5c2

N-CH2-CH2-O

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