Reaktion #65119

ord-bd8175091f0e4c5691795727be49dd1c

Reaktionsgleichung

C[C@]12C[C@H](N3CCCCC3)[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](N3CCCCC3)C[C@@H]12
(2β,3α,5α,16β)-3-hydroxy-2,16-di-(1-piperidinyl)-androstan-17-one
CC(=O)Cl
acetylchloride
→
CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@H](CC[C@]4(C)C(=O)[C@@H](N5CCCCC5)C[C@@H]34)[C@@]2(C)C[C@@H]1N1CCCCC1
(2β,3α,5α,16β)-3-acetyloxy-2,16-di-(1-piperidinyl)androstan-17-one

Edukte

C[C@]12C[C@H](N3CCCCC3)[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)[C@@H](N3CCCCC3)C[C@@H]12
(2β,3α,5α,16β)-3-hydroxy-2,16-di-(1-piperidinyl)-androstan-17-one
CC(=O)Cl
acetylchloride

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeevaporated to dryness
  2. 2
    workup.DISSOLUTIONThe residue was dissolved in toluene
  3. 3
    Sonstigethe solution again evaporated to dryness
  4. 4
    workup.DISSOLUTIONthe residue dissolved in dichloromethane
  5. 5
    WaschenThe solution was washed with saturated aqueous sodium carbonate solution, with water and with saturated brine
  6. 6
    Trocknendried over sodium sulphate
  7. 7
    Sonstigeevaporated to dryness

Vorschrift

To a stirred solution of 40 g of (2β,3α,5α,16β)-3-hydroxy-2,16-di-(1-piperidinyl)-androstan-17-one in 160 ml of dichloromethane were added 13.5 ml of acetylchloride at 15°-20 ° C. The solution was stirred for 6 h at room temperature and thereafter evaporated to dryness. The residue was dissolved in toluene, the solution again evaporated to dryness and the residue dissolved in dichloromethane. The solution was washed with saturated aqueous sodium carbonate solution, with water and with saturated brine, dried over sodium sulphate, and evaporated to dryness to give 43.5 g of (2β,3α,5α,16β)-3-acetyloxy-2,16-di-(1-piperidinyl)androstan-17-one. Mp 154° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05418226uspto-grants-1995_05