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(Diethylamino)sulfur trifluoride → (4R,9aR)-6-Fluoromethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11945
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11945
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][C:15]([N:17]1[CH2:29][C@@H:28]([CH3:30])[N:27]2[C@H:19]([CH2:20][C:21]3[C:26]2=[N:25][C:24]([CH2:31]OCCO)=[CH:23][CH:22]=3)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>ClCCl>[C:10]([O:14][C:15]([N:17]1[CH2:29][C@@H:28]([CH3:30])[N:27]2[C@H:19]([CH2:20][C:21]3[C:26]2=[N:25][C:24]([CH2:31][F:7])=[CH:23][CH:22]=3)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]
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Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 69557393(4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester2×

Produkt 1

HCID 69360199(4R,9aR)-6-Fluoromethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A solution of 82.0 μl (0.11 g, 0.63 mmol) diethylaminosulphur trifluoride in 2 ml dichloromethane was cooled to −78 deg C. and treated with a solution of 0.20 g (0.63 mmol) (4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 15, intermediate b) in 2 ml dichloromethane. The cooling bath was removed and the reaction stirred for 1 h at room temperature. The solution was extracted with 10% aqueous sodium bicarbonate solution, washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:2) as eluant to afford the desired compound as a colorless oil (51.7%).

Aufarbeitung

  1. customThe cooling bath was removed
  2. extractionThe solution was extracted with 10% aqueous sodium bicarbonate solution
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (0.032–0.063 mm) with ethyl acetate:n-hexane (1:2) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-02cf394ff1174a2c8c2dd1ba46ed3904
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07098337B2

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