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Hexachloroethane → (2R,6S)-4-(2-((tert-Butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

HRID 245375
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Reaktionsgleichung

Reaktionsgleichung von HRID 245375
C(NC(C)C)(C)C.C([Li])CCC.[Si:13]([O:30][CH2:31][C:32]1[C:37]([N:38]2[CH2:43][C@H:42]([CH3:44])[O:41][C@H:40]([CH3:45])[CH2:39]2)=[CH:36][C:35]([F:46])=[CH:34][N:33]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl:47]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOC(C)=O>[Si:13]([O:30][CH2:31][C:32]1[C:37]([N:38]2[CH2:39][C@H:40]([CH3:45])[O:41][C@H:42]([CH3:44])[CH2:43]2)=[C:36]([Cl:47])[C:35]([F:46])=[CH:34][N:33]=1)([C:26]([CH3:27])([CH3:29])[CH3:28])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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Komponenten

7

Edukt 4

HCID 6214HexachloroethaneHCID 7912DiisopropylamineHCID 67318917(2R,6S)-4-(2-((tert-butyldiphenylsilyloxy)methyl)-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine2×HCID 178418339Butyllithium

Produkt 1

HCID 67319975(2R,6S)-4-(2-((tert-Butyldiphenylsilyloxy)methyl)-4-chloro-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of diisopropylamine (3.51 ml, 24.65 mmol) in THF (30 ml) was cooled in a dry ice-acetone bath. A solution of n-butyllithium (2.5 M in hexanes, 9.28 ml, 23.20 mmol) was added and the mixture was warmed to 0° C. and recooled in a dry ice-acetone bath. The solution was added to a second solution of (2R,6S)-4-(2-((tert-butyldiphenylsilyloxy)methyl)-5-fluoropyridin-3-yl)-2,6-dimethylmorpholine (Intermediate 44, 6.94 g, 14.50 mmol) in THF (30 ml) cooled in a dry ice-acetone bath. The mixture was stirred for 45 minutes before the solution was transferred via cannula to a solution of hexachloroethane (2.79 ml, 24.65 mmol) in 60 ml THF also cooled in a dry ice-acetone bath. The mixture was allowed to warm to room temperature before being diluted with EtOAc and washed with water and brine. The combined aqueous layers were extracted again with EtOAc, which was washed with brine. Drying (MgSO4) of the combined EtOAc extracts and removal of solvent gave a gummy solid that was chromatographed on silica gel (50% hexanes in CH2Cl2 followed by gradient elution to 100% CH2Cl2) to afford product as an oil that slowly solidified (5.26 g yield). MS (ES) MH+: 513 for C28H34ClFN2O2Si.

Aufarbeitung

  1. customrecooled in a dry ice-acetone bath
  2. temperaturecooled in a dry ice-acetone bath
  3. temperaturealso cooled in a dry ice-acetone bath
  4. temperatureto warm to room temperature
  5. washwashed with water and brine
  6. extractionThe combined aqueous layers were extracted again with EtOAc, which
  7. washwas washed with brine
  8. customDrying
  9. custom(MgSO4) of the combined EtOAc extracts and removal of solvent
  10. customgave a gummy solid
  11. customthat was chromatographed on silica gel (50% hexanes in CH2Cl2 followed by gradient elution to 100% CH2Cl2)
  12. customto afford product as an oil that
  13. custom(5.26 g yield)

Quellen und Nachweise

ORD-Eintrag
ord-91d0063838904f9b9766986e5c6d8150
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658641B2

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