반응 #459011

ord-6fa81d89cb204e4faf0ed5d65bbfc46c

반응 방정식

C[C@H]1CC2(C=C3CC[C@H]4[C@@H]5CC[C@H](O)[C@@]5(C)CC[C@@H]4[C@]31CO)OCCS2
17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal
→
C[C@H]1CCC=C2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@]21CO
1α-methyl-4-androstene-17β,19-diol

반응물

C[C@H]1CC2(C=C3CC[C@H]4[C@@H]5CC[C@H](O)[C@@]5(C)CC[C@@H]4[C@]31CO)OCCS2
17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal

시약

[Ni]
Raney nickel

용매

CO
methanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도the resulting suspension is refluxed for 4 hours with rapid stirring
  2. 2
    온도The suspension is cooled
  3. 3
    여과filtered
  4. 4
    기타the solvent evaporated
  5. 5
    기타The remaining residue is chromatographed on silica gel
  6. 6
    세척an eluted with methylenechloride
  7. 7
    기타Recrystallization from acetone-hexane

실험 절차

Raney nickel is added to a solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal in methanol and the resulting suspension is refluxed for 4 hours with rapid stirring. The suspension is cooled, filtered and the solvent evaporated. The remaining residue is chromatographed on silica gel an eluted with methylenechloride. Recrystallization from acetone-hexane yields the compound 1α-methyl-4-androstene-17β,19-diol.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04087524uspto-grants-1978_05