Benzoic Acid → (1S,4aS,7aR)-7-(hydroxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

HRID 1976372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976372
[CH3:1][O:2][C:3]([C:5]1[CH:6]2[CH2:18][CH:17]=[CH:16][CH:7]2[CH:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4].[C:19](O)(=[O:26])C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:18][CH:17]=[C:16]([CH2:19][OH:26])[C@@H:7]2[C@H:8]([O:11][C:12](=[O:15])[NH:13][CH3:14])[O:9][CH:10]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 243Benzoic AcidHCID 2724141Tetrabutylammonium FluorideHCID 867566731-(Methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

Produkt 1

HCID 57107324(1S,4aS,7aR)-7-(hydroxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylesterAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

28.5 g of the above (1S, 4aS, 7aR )-7-(tert-butyldiemthylsilyloxymethyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester were dissolved in tetrahydrofuran followed by addition of 35 g of benzoic acid. Next, 143 ml of tetra-n-butylammonium fluoride (1.0 M, tetrahydrofuran solution) were dropped in followed by stirring for 24 hours at room temperature. The reaction mixture was then extracted with ethyl acetate. After washing the organic phase with saturated aqueous sodium bicarbonate and brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ether eluate in the form of (1S,4aS,7aR)-7-(hydroxy-methyl)-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (20.0 g, yield: 98.4%). The physicochemical properties of this compound are described in Table 66, Compound No. I-315.

Aufarbeitung

  1. extractionThe reaction mixture was then extracted with ethyl acetate
  2. washAfter washing the organic phase with saturated aqueous sodium bicarbonate and brine, it
  3. dry with materialwas dried over magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3b59b4c262f44436a8acc50fd5538f92
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06225478B1

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