Reaktion #92664

ord-1cff756c6f4b46999d9fa25a03a809ec

Reaktionsgleichung

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]4OC45C[C@@H](O)CC[C@]5(C)[C@H]3CC[C@]12C
5,6α-epoxicholestan-3β-ol
NCCc1c[nH]c2ccccc12
tryptamine
CCCCO
1-Butanol
→
CCCN[C@@H]1C[C@H]2[C@@H]3CC[C@H]([C@H](C)CCCC(C)C)[C@@]3(C)CC[C@@H]2[C@@]2(C)CC[C@H](O)C[C@]12O
5α-Hydroxy-6β-(3-propylamino)-cholestan-3β-ol
Ausbeute 71.5%

Edukte

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]4OC45C[C@@H](O)CC[C@]5(C)[C@H]3CC[C@]12C
5,6α-epoxicholestan-3β-ol
NCCc1c[nH]c2ccccc12
tryptamine
CCCCO
1-Butanol

Reagenzien

Keine

Lösungsmittel

COC(C)(C)C
methyl-tertbutyl-ether

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeequipped with a magnetic stirrer bar
  2. 2
    Temperaturthe mixture heated
  3. 3
    Temperaturto reflux for 40 h
  4. 4
    Waschenwashed with water (5 vol) and with brine (5 vol)
  5. 5
    Wascheneluted with methyl-tertbutyl-ether (3 vol)
  6. 6
    Sonstigethe solvent was removed under reduced pressure

Vorschrift

5,6α-epoxicholestan-3β-ol (8.9 g, 22.1 mmol, 1 eq) and tryptamine (7.1 g, 44.1 mmol, 2 eq) were charged in a round-bottomed flask equipped with a magnetic stirrer bar. 1-Butanol (70 ml, 5 vol) was added and the mixture heated to reflux for 40 h. The reaction mixture was cooled at r.t., diluted with methyl-tertbutyl-ether (5 vol) and washed with water (5 vol) and with brine (5 vol). The organic layer was passed through a silica pad (40 g) eluted with methyl-tertbutyl-ether (3 vol) then 10% Methanol/ethyl acetate (60 vol). Fractions of interest were pooled and the solvent was removed under reduced pressure to give 5α-Hydroxy-6β-(3-propylamino)-cholestan-3β-ol as a white solid (7.3 g, 59%). In same conditions, use of ethanol as solvent (40 vol) and Ca(OTf)2 as catalyst gave a 21% yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447141B2uspto-grants-2016_09