Keto-pantoyllactone → D-Pantolactone

HRID 1638413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638413
[CH3:1][C:2]1([CH3:9])[C:7](=[O:8])[C:5](=[O:6])[O:4][CH2:3]1.CS(N1C[C@@H](P(C2CCCCC2)C2CCCCC2)C[C@H]1CP(C1C=CC=CC=1)C1C=CC=CC=1)(=O)=O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[C@@H:7]([OH:8])[C:5](=[O:6])[O:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 39Keto-pantoyllactoneHCID 13665148(2S,4S)-N-methanesulfonyl-4-dicyclohexylphosphino-2-diphenylphosphinomethylpyrrolidine

Produkt 1

HCID 439368D-PantolactoneAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To 50 ml of benzene were added 12.8 g (100 m-mol) of ketopantolactone, 1 mg (0.0025 m-mol) of rhodium 1,5-hexadiene chloride complex compound and 3.0 mg (0.0055 m-mol) of (2S,4S)-N-methanesulfonyl-4-dicyclohexylphosphino-2-diphenylphosphinomethylpyrrolidine (MSCPM) obtained in Example 1(h). An autoclave equipped with a stirrer, a pressure gauge and a thermometer was charged with the above mixture and a treatment was carried out in the same manner as described in Example 13 whereby 12.4 g (yield: 95%) of D-pantolactone was obtained. [α]D =-42.1° (optical yield: 82.5%)

Aufarbeitung

  1. customAn autoclave equipped with a stirrer
  2. additiona pressure gauge and a thermometer was charged with the above mixture

Quellen und Nachweise

ORD-Eintrag
ord-e77886d0b3b64bbbb19fd851d9afdbb2
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04879389

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