Reaktion #516885

ord-bd0f7d1f36db4ac781327365cb4c7f60

Reaktionsgleichung

CC(C)CCC[C@@H](C)[C@H]1CCC2C3CC=C4CC(OC(=O)Cl)CC[C@]4(C)C3CC[C@@]21C
cholesteryl chloroformate
CN(C)CCN
N,N-dimethylethylenediamine
II
iodine
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)NCCN(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
Compound XIV
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)NCCN(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
3β[N-(N′,N′-dimethylaminoethane)-carbamoyl]cholesterol

Edukte

CC(C)CCC[C@@H](C)[C@H]1CCC2C3CC=C4CC(OC(=O)Cl)CC[C@]4(C)C3CC[C@@]21C
cholesteryl chloroformate
CN(C)CCN
N,N-dimethylethylenediamine
II
iodine

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform
ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent and the unreacted amine were removed in vacuo
  2. 2
    SonstigeCompound XIV was purified by two successive recrystallizations in ethanol
  3. 3
    Sonstige(Yield, 65%) TLC (chloroform:methanol=65:35)

Vorschrift

Compound XIV was synthesized by mixing absolution of cholesteryl chloroformate (0.5 mmol) in chloroform with a solution of N,N-dimethylethylenediamine (9.1 mmol) in chloroform in a dry ice-ethanol bath. The solvent and the unreacted amine were removed in vacuo. Compound XIV was purified by two successive recrystallizations in ethanol. (Yield, 65%) TLC (chloroform:methanol=65:35) showed a single spot (Rf=0.37) when developed with iodine. The product was characterized by proton NMR.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06319516B1uspto-grants-2001_11