Methanol → (1R*,2R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 2088093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088093
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:10](=[O:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C1COCC1>[CH3:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1].[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:17])=[O:18])[CH2:15][C@@:9]1([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:10]([OH:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 69889408(1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one

Produkt 2

HCID 78922-MethylpentaneHCID 69890353(1R*,2R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-olAusbeute 193,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(1R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-one (Description 3; 3.05 g, 7.03 mmol) was dissolved in hot THF (10 ml) and methanol (150 ml) was added. The mixture was heated at reflux for 2 minutes and cooled to +5° C. Sodium borohydride (600 mg, 15.8 mmol) was added. The reaction mixture was stirred for 20 minutes at +5° C. The cooling bath was removed and the mixture was stirred for 90 minutes at ambient temperature. Saturated aqueous NaHCO3 (10 ml) was added and the mixture was concentrated in vacuo. The residue was treated with water and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The solid residue was crystallised from acetone:iso-hexane to give the title compound (2.95 g, 97%) as white crystals.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 minutes
  3. temperaturecooled to +5° C
  4. customThe cooling bath was removed
  5. stirringthe mixture was stirred for 90 minutes at ambient temperature
  6. additionSaturated aqueous NaHCO3 (10 ml) was added
  7. concentrationthe mixture was concentrated in vacuo
  8. additionThe residue was treated with water
  9. extractionextracted with ethyl acetate (3×50 ml)
  10. dry with materialThe combined organic extracts were dried (Na2SO4)
  11. concentrationconcentrated
  12. customThe solid residue was crystallised from acetone

Quellen und Nachweise

ORD-Eintrag
ord-6eb30258c2dd45869c5b9f520f72906e
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

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