Formaldehyde → 17beta-[N-Methyl-N-(2-dimethylaminoethoxy)amino]methyl-5beta-androstane-3beta,14beta-diol

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Reaction Steps

To a stirred solution of 0.41 g of 17β-(2-dimethylaminoethoxyamino)methyl-5β-androstane-3β,14β-diol (I-am) and 1.0 ml of 37% aqueous formaldehyde in 10 ml of acetonitrile 0.20 g of NaBH3CN was added. The reaction was stirred for 28 hr and then diluted with 0.1N hydrochloric acid and extracted with ethyl acetate. The aqueous layer was basified to pH 9.5 with 2.5N NaOH and extracted with ethyl acetate; the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using chloroform/methanol/26% aqueous ammonium hydroxide 90/9/1 as the eluant; the fractions containing the title compound were collected and evaporated to dryness under reduced pressure. The residue was dissolved with ethyl acetate and the stoichiometric amount of oxalic acid was added to give 0.33 g of the title compound (I-ap), as a white solid, oxalate.

Provenance & Evidence