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Details for Patent: 4,179,453

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Details for Patent: 4,179,453

Title: Process for preparing 17.beta.-carboxy-5-androsten-3-ones
Abstract:A process for preparing 17.beta.-carboxy-4-androsten-3-ones comprising the steps of (1) reacting a 17.beta.-(1-ketoethyl)-5-androsten-3-ol, for example, pregnenolene, with pyridine and iodine to form a pyridinium iodide compound; (2) reacting the pyridinium iodide compound with alkali metal methoxide in methanol to form a methyl-5-androsten-3-ol-17.beta. carboxylate; (3) oxidizing the product of Step (2) preferably with aluminum isopropoxide to form methyl-4-androsten-3-one-17.beta.-carboxylate; and (4) hydrolyzing the product of Step (3) to the corresponding 17.beta.-carboxylic acid, salt, or ester. The 17.beta.-carboxy-4-androsten-3-ones are useful as intermediates for preparation of N-substituted-17.beta.-carbamoylandrost-4-en-3-one and 4-aza-17.beta.-substituted-5.alpha.-androstan-3-one 5.alpha. reductase inhibitors.
Inventor(s): Johnston; David B. R. (Warren, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Filing Date:Apr 13, 1978
Application Number:05/896,120
Claims:1. A method for preparing a 17.beta.-carboxy-4-androsten-3-one having the formula: ##STR3## where R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are the same or different and are hydrogen or lower alkyl;

R.sup.7 is hydrogen or cyano;

M is hydrogen, lower alkyl, or alkali metal;

Z is CH--R.sup.9 where R.sup.9 is hydrogen, .alpha.-fluoro, or .alpha.-lower alkyl; and the dotted line between positions 1 and 2 represents the possibility of a single bond when Z is CH--R.sup.9 and a double bond when Z is C--R.sup.9 ; comprising the steps of

(1) reacting a 17.beta.-(1-ketoethy)-5-androsten-3-ol with pyridine and iodine to form a pyridinium iodide compound;

(2) reacting the pyridinium iodide compound with alkali metal methoxide in methanol to form a methyl-5-androsten-3-ol-17.beta.-carboxylate;

(3) oxidizing the 5-androsten-3-ol to form methyl-4-androsten-3-one-17.beta.-carboxylate; and

(4) hydrolyzing the methyl-17.beta.-carboxylate to the corresponding 17.beta.-carboxylic acid.

2. The method of claim 1 wherein in the third step the oxidizing is carried out using aluminum isopropoxide and cyclohexanone.

3. The method of claim 1 wherein in the fourth step the hydrolyzing is carried out using potassium hydroxide in a mixture of methanol and water.

4. A method for preparing methyl 5-androsten-3-ol-17.beta.-carboxylates having the formula: ##STR4## where R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are the same or different and are hydrogen or lower alkyl;

R.sup.7 is hydrogen or cyano;

M is hydrogen, lower alkyl, or alkali metal;

Z is CH--R.sup.9 where R.sup.9 is hydrogen, .alpha.-fluoro, or .alpha.-lower alkyl; and the dotted line between positions 1 and 2 represents the possibility of a single bond when Z is CH--R.sup.9 and a double bond when Z is C--R.sup.9 ; comprising the step of reacting a compound of the formula: ##STR5## wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and Z have the same meaning as above, with alkali metal methoxide in methanol.
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