Hydrochloric Acid → (1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 2088128

Reaktionsgleichung

Reaktionsgleichung von HRID 2088128
[CH2:1]([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:10]([O:16][Si](CC)(CC)CC)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([N:8]1[C@@H:13]2[CH2:14][CH2:15][C@@:9]1([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:10]([OH:16])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 69889465(1R,2R,5R)-8-Benzyl-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane

Produkt 1

HCID 69688994(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-olAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of (1R,2R,5R)-8-benzyl-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane (Description 52; 107 mg, 0.26 mmol), 2M hydrochloric acid (3 ml) and methanol (6 ml) was stirred at +55° C. for 15 minutes, then concentrated in vacuo and quenched with saturated aqueous NaHCO3. The mixture was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated to give the title compound (79 mg, 96%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customquenched with saturated aqueous NaHCO3
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5f68bde183be42919f6aa0c26159c787
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

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