(1S,4aS,6S,7R,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta [c]-pyrane-4-carboxylic acid benzyl ester → (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid

HRID 1976355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976355
C([O:8][C:9]([C:11]1[C@H:12]2[CH2:24][C@@H:23]3[O:25][C@:22]3([CH3:26])[C@@H:13]2[C@H:14]([O:17][C:18](=[O:21])[NH:19][CH3:20])[O:15][CH:16]=1)=[O:10])C1C=CC=CC=1>[C].[Pd].C(OCC)(=O)C>[O:25]1[C@@:22]2([CH3:26])[C@@H:23]1[CH2:24][C@@H:12]1[C:11]([C:9]([OH:10])=[O:8])=[CH:16][O:15][C@@H:14]([O:17][C:18](=[O:21])[NH:19][CH3:20])[C@H:13]12

Komponenten

4

Edukt 1

HCID 57263744(1S,4aS,6S,7R,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta [c]-pyrane-4-carboxylic acid benzyl ester

Produkt 1

HCID 18397301(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acidAusbeute 113,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

35 mg of 5% palladium-carbon catalyst were added to an ethyl acetate solution containing 350 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta [c]-pyrane-4-carboxylic acid benzyl ester followed by stirring for 2 hours at room temperature under hydrogen gas atmosphere at 1 atm. After filtering out the insoluble matter, the filtrate was concentrated under reduced pressure to obtain a colorless powder in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy) cyclopenta [c]-pyrane-4-carboxylic acid (298 mg, yield: 99%). The physicochemical properties of this compound are described in Table 1, Compound No. 1.

Aufarbeitung

  1. filtrationAfter filtering out the insoluble matter
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d28a546e96b442a3a8563a5e5dcf4453
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225478B1

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