(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 377072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377072
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-33fc9eeb98244a179812c4bf88624d62
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022888

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