Reacción #417138

ord-c5a64f943f3e4db88c7d98b09311a238

Ecuación de reacción

CC(=O)Cl
Acetyl chloride
C[C@]12C[C@H](N3CCOCC3)[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)[C@@H](N3CCCC3)C[C@@H]12
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1pyrrolidinyl)-androstane-3,17-diol
ClCCl
dichloromethane
O=C([O-])O.[K+]
potassium bicarbonate
→
CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C)[C@H]3C[C@H](N3CCCC3)[C@@H]4OC(C)=O)[C@@]2(C)C[C@@H]1N1CCOCC1
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1pyrrolidinyl)-androstane-3,17-diol diacetate

Reactantes

CC(=O)Cl
Acetyl chloride
C[C@]12C[C@H](N3CCOCC3)[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)[C@@H](N3CCCC3)C[C@@H]12
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1pyrrolidinyl)-androstane-3,17-diol
ClCCl
dichloromethane
O=C([O-])O.[K+]
potassium bicarbonate

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto give pH>7
  2. 2
    Otrothe dichloromethane layer was separated
  3. 3
    Lavadowashed with water (3×150 ml)
  4. 4
    Secadodried (Na2SO4)
  5. 5
    Otroevaporated to dryness

Procedimiento

Acetyl chloride (10.0 ml) was added to a stirred suspension of (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1pyrrolidinyl)-androstane-3,17-diol (10.0 g) in dichloromethane (100 ml). After 24 h. at room temperature, saturated potassium bicarbonate solution (approx. 20 ml) was added to give pH>7; the dichloromethane layer was separated, washed with water (3×150 ml), dried (Na2SO4) and evaporated to dryness to afford (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1pyrrolidinyl)-androstane-3,17-diol diacetate as an off-white froth (7.78 g), [α]D20 =+11.4° (c 0.57 in CHCl3)

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04894369uspto-grants-1990_01