StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Bicarbonate → (1S,3aS,7aR)-1-acetoxymethyl-5-[(Z)-3-hydroxypropyliden]-7a-methylperhydroinden-3a-ol

HRID 725180
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 725180
[C:1]([O:4][CH2:5][C@@H:6]1[C@:14]2([CH3:15])[C@@:9]([OH:23])([CH2:10]/[C:11](=[CH:16]\[CH2:17][CH:18]3OCC[O:19]3)/[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(=[O:3])[CH3:2].C([O-])(O)=O.[Na+]>CC1C=CC(S(O)(=O)=O)=CC=1.C(#N)C.O>[C:1]([O:4][CH2:5][C@@H:6]1[C@:14]2([CH3:15])[C@@:9]([OH:23])([CH2:10]/[C:11](=[CH:16]\[CH2:17][CH2:18][OH:19])/[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 70050966(1S,3aS,7aR)-1-acetoxymethyl-5-((Z)-2-(1,3-dioxolan-2-yl)ethyliden]-7a-methylperhydroinden-3a-ol

Produkt 1

HCID 70049687(1S,3aS,7aR)-1-acetoxymethyl-5-[(Z)-3-hydroxypropyliden]-7a-methylperhydroinden-3a-olAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidLösungsmittel
HCID 18373917
Acetonitrile--water (1/1)
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1.80 g of (1S,3aS,7aR)-1-acetoxymethyl-5-((Z)-2-(1,3-dioxolan-2-yl)ethyliden]-7a-methylperhydroinden-3a-ol in 20 ml of 1N PTSA in acetonitrile/water 85:15 was kept at room temperature for 8 hrs. The mixture was then neutralised with 5% aqueous NaHCO3, concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was dissolved in 5 ml of methanol and the solution cooled at 0° C. 0.33 g of NaBH4 were cautiously added and the mixture was stirred for 1 hr. It was then diluted with 10 ml of 5% aqueous NaH2PO4.H2O and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give 1.13 g of (1S,3aS,7aR)-1-acetoxymethyl-5-[(Z)-3-hydroxypropyliden]-7a-methylperhydroinden-3a-ol as a dense colourless off.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in 5 ml of methanol
  6. addition0.33 g of NaBH4 were cautiously added
  7. additionIt was then diluted with 10 ml of 5% aqueous NaH2PO4.H2O
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-78b736c3e19a4cf8b3afa6189cdf625c
Quelldatensatz
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05705531

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion