Methyl morpholine oxide → (R,R)-Hydrobenzoin

HRID 1267721

Reaktionsgleichung

Reaktionsgleichung von HRID 1267721
C[N+]1([O-])CC[O:5]CC1.[C:9]1(/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH2:23].CC(C)=O.C(#N)C>[O-][Os](=O)(=O)=O.O=[Os](=O)(=O)=O>[C:9]1([C@@H:15]([OH:5])[C@@H:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[OH:23])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 82029Methyl morpholine oxideHCID 638088trans-StilbeneHCID 18799168Acetonitrile acetone water

Produkt 1

HCID 853019(R,R)-HydrobenzoinAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 9543328OsmateKatalysator

Versuchsvorschrift

Resin-OsO4 (0.01 Eq. Wt.), Hydroquinidine 1,4-phthalazinediyl diether (DHQD)2PHAL (0.01 Eq. Wt.) and N-methylmorpholine-N-oxide (1.5 Eq. Wt.) were stirred in the mixed solvent of water/acetone/acetonitrile (in the volume ratio of 1:1:1). To this mixture was added trans-stilbene (1.0 Eq. Wt) and stirred at room temperature for 6 hours. After the reaction, supported osmate catalyst was filtered off and washed with methanol. The combined filtrates were concentrated under reduced pressure. The chiral ligand was recovered from the aqueous layer after acidification (1N HCl). The pure product was obtained by removing the solvent at reduced pressure followed by column chromatography. (R,R)-(+)-1,2-diphenyl-1,2-ethandiol of more than 99.0% of enantiomeric excess was obtained (yield 96%) [∝]D +92.44 (c1.0, EtOH): e.e.=99.4%

Aufarbeitung

  1. customAfter the reaction
  2. filtrationwas filtered off
  3. washwashed with methanol
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customThe chiral ligand was recovered from the aqueous layer after acidification (1N HCl)
  6. customThe pure product was obtained
  7. customby removing the solvent at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-259e8b4c247b4b0daa93b49d2cbaca26
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552234B1

Verknüpfte Notizen

Wird geladen…