Reaction #928

ord-4fe7e7b0295444c08046dd75241f89c9

Reaction equation

C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
steroid
C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
2-Hydroxyimino-17β-hydroxy-5α-androstan-3-one
Cl.NO
NH2OH.HCl
CC(=O)[O-].O.[Na+]
NaOAc H2O
→
CC(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=NO)C(=NO)C[C@]4(C)[C@H]3CC[C@]12C
17β-Acetoxy-2,3-dihydroxyimino-5α-androstane

Reactants

C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
steroid
C[C@]12CC(=NO)C(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
2-Hydroxyimino-17β-hydroxy-5α-androstan-3-one
Cl.NO
NH2OH.HCl
CC(=O)[O-].O.[Na+]
NaOAc H2O

Reagents

None

Solvents

O
H2O

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed for 20 minutes
  2. 2
    FiltrationThe precipitate was collected by filtration
  3. 3
    WashThe resulting solid 8 was washed with H2O and air
  4. 4
    Otherdried

Procedure

A suspension of steroid 7, NH2OH.HCl and NaOAc/H2O was refluxed for 20 minutes. The reaction was cooled to room temperature and poured into H2O. The precipitate was collected by filtration. The resulting solid 8 was washed with H2O and air and dried; wt. 23.4 g.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723455uspto-grants-1998_03