Bromomethylcyclopropane → 1-[(2beta,3alpha,5beta,16alpha,17beta)-3,17-Bis(acetyloxy)-2-(4-morpholinyl)-androstan-16-yl]-1-(cyclopropylmethyl)pyrrolidinium bromide

Participants

Reaction Steps

Cyclopropylmethyl bromide (1.0 ml) was added to a solution of (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol diacetate (2.0 g) in acetonitrile (20 ml) and the solution was heated under reflux for 14 d. Evaporation of the reaction mixture to dryness under reduced pressure gave a pale brown solid (2.30 g), which was crystallised from dichloro-methanediethyl ether to remove most of the unreacted starting material. Further purification, by chromatography on alumina as described above, gave material, which was dissolved in dichloro-methane and precipitated from the solution with diethyl ether to give 1-[(2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)-2-(4-morpholinyl)-androstan-16-yl]-1-(cyclopropylmethyl) pyrrolidinium bromide, m.p. decomposes above 175° C.; [α]D20 =-11.6° (c 0.66 in CHCl3).

Provenance & Evidence