Toluene → 3alpha-Hydroxy-21-[2'-morpholinoethylthio]-5alpha-pregnane-11,20-dione

Participants

Reaction Steps

2-Morpholinoethanethiol (1 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of dry toluene (30 ml.) and isopropyl alcohol (25 ml.). After 5 min., 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (2.0 g.) was added and the resulting mixture was stirred at 40° for 30 min. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. (EtOAc) to give title compound (150 mg.) as a white foam, [α]D + 73° (c 0.9); λmax. 243 nm. (ε 570).

Provenance & Evidence