Keto-pantoyllactone → D-Pantolactone

HRID 1906588

Reaktionsgleichung

Reaktionsgleichung von HRID 1906588
O=O.[CH3:3][C:4]1([CH3:11])[C:9](=[O:10])[C:7](=[O:8])[O:6][CH2:5]1.CC(OC(N1[C@H](CP(C2C=CC=CC=2)C2C=CC=CC=2)C[C@H](P(C2C=CC=CC=2)C2C=CC=CC=2)C1)=O)(C)C.FC(F)(F)C([O-])=O.C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:3][C:4]1([CH3:11])[C@@H:9]([OH:10])[C:7](=[O:8])[O:6][CH2:5]1

Komponenten

6

Edukt 4

HCID 39Keto-pantoyllactoneHCID 977OxygenHCID 3084618N,N,N-Tributylbutan-1-aminium trifluoroacetateHCID 10209545(2S,4S)-(-)-N-BOC-4-Diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine

Produkt 1

HCID 439368D-Pantolactone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 500 ml steel autoclave was loaded in a glove box (O2 -content less than 1 ppm) with 40.0 g (0.31 mol) of ketopantolactone, 210 ml of toluene, 180.6 mg (0.389 mmol) of [Rh(COD)2 ]PF6, 237.3 mg (0.389 mmol) of mCH3 --BPPM and 138.3 mg (0.389 mmol) of tetrabutylammonium trifluoroacetate. The hydrogenation was carried out at a constant pressure of 40 bar of H2 at 30° C. and with intensive stirring. By virtue of the exothermic reaction the temperature rose to 55° C. A conversion of above 99% was achieved after 1.2 hours. After a total hydrogenation time of 2 hours the mixture was worked-up as described in Example 2. Pure (R)-pantolactone was obtained. [α]D20 =-46.0°. Optical purity 89.1%.

Aufarbeitung

  1. customwas carried out at a constant pressure of 40 bar of H2 at 30° C. and with intensive stirring
  2. customBy virtue of the exothermic reaction the temperature
  3. customrose to 55° C
  4. customAfter a total hydrogenation time of 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-c20e25a16536471ca51a82d1ff149b83
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04652657

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