Ethyl Acetate → (4R,9aR)-6-(3-Hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11920

Reaktionsgleichung

Reaktionsgleichung von HRID 11920
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]=[CH:23][C:24](OCC)=[O:25])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 69557653(4R,9aR)-6-(2-Ethoxycarbonyl-vinyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 69556846(4R,9aR)-6-(3-Hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 245.0 mg (0.63 mmol) (4R,9aR)-6-(2-ethoxycarbonyl-vinyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 12, intermediate) in 10 ml diethyl ether were added 50.0 mg (1.32 mmol) lithium aluminium hydride. After 2 h the reaction mixture was poured into saturated aqueous potassium sodium tartrate solution and ethyl acetate then filtered through a short pad of dicalite speed plus. The aqueous phase was extracted four times with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane as eluant to afford the compound as a colorless solid (50.5%).

Aufarbeitung

  1. filtrationthen filtered through a short pad of dicalite speed plus
  2. extractionThe aqueous phase was extracted four times with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (0.032–0.063 mm) with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c76cc796d2ea4b6895678bcd5aed63a0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098337B2

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