Norethandrolone

Chemical Name 7-Chloro-1 -dihydro-5-phenyl-l (2H)-1,4-benzodiazepin-2-one Common Name Nordiazepam desmethyidiazepam Structural Formula  

A solution of 3.1 g of (2-benzoyl-4-chlorophenyl-carbamoylmethyl)carbamic acid benzyl ester in 30 cc of 20% hydrobromic acid in glacial acetic acid was stirred for 45 minutes at room temperature. On addition of 175 cc of anhydrous ether, a gummy solid precipitated. After several minutes the ether solution was decanted. The resultant 5-chloro-2-gly-cylaminobenzophenone was not isolated, but about 155 cc of ether was added to the residue and after chilling in an ice bath, 10% sodium hydroxide was added until the mixture was alkaline. The ether layer was then separated, washed twice with water and dried over sodium sulfate. After filtration, the ether solution was concentrated to dryness in vacuo. The residue was crystallized from benzene to yield 7-chloro-5-phenyl-3H-1 /i-benzodiazepin-2(1H)-one. 

Stempel, A. U.S. Patent 3,202,699 August 24,1965 assigned to Hoffmann-LaRoche Inc. 

Chemical Abstracts Registry No. 1088-11 -5 Trade Nama Manufacturer 

Therapeutic Function Androgen Chemical Nama 17-Hydroxy-19-norpregn-4-ene-3-one Common Name -Structural Formula  

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Reaction of estrone methyl ether with methyl Grignard reagent followed by Birch reduction and hydrolysis of the intermediate enol ether affords the prototype orally active androgen in the 19-nor series, normethandrolone (69). ° (Note that here again the addition of the methyl group proceeded stereoselectively by approach from the least hindered side.) The preparation of the ethyl homolog starts by catalytic reduction of mestranol treatment of the intermediate, 70, under the conditions of the Birch reduction and subsequent hydrolysis of the intermediate enol ether yields norethandrolone (71). ... 

The synthesis of the homologue norethandrolone starts with catalytic reduction of the side chain unsaturation in mestranol (9-1) to the corresponding ethyl derivative... 

On the way to prepare metabolites of equine norethandrolone, a Reformatsky reaction has been applied to epiandrosterone acetate 44 in refluxing benzene the authors succeeded... 

G. Carignan and B. A. Lodge, Comparative study of the applications of gas-liquid and high-performance liquid chromatography to the analysis of norethandrolone, J. Chromatogr., 779 184 (1979). 

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