Acetone → 3-Benzyldecahydro-1,5-methanocyclopenta[d]azepine-6,7-diol

HRID 1727190

Reaktionsgleichung

Reaktionsgleichung von HRID 1727190
[C:1]1([CH2:7][N:8]2[CH2:17][CH:16]3[CH2:18][CH:10]([CH:11]4C3C=C[CH2:12]4)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:23]CC1.[O-][Si]([O-])=O.[Mg+2].S([O-])(O)=O.[Na+].[CH3:37][C:38]([CH3:40])=[O:39]>[Os](=O)(=O)(=O)=O>[C:1]1([CH2:7][N:8]2[CH2:17][CH:16]3[CH2:18][CH:10]([CH:11]4[CH:40]3[CH:38]([OH:39])[CH:37]([OH:23])[CH2:12]4)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 5

HCID 180AcetoneHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 598378489-Benzyl-9-aza-tricyclo[5.3.1.02,6]undec-3-ene

Produkt 1

HCID 598378623-Benzyldecahydro-1,5-methanocyclopenta[d]azepine-6,7-diolAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 30318Osmium TetroxideKatalysator

Versuchsvorschrift

A solution of 9-(phenylmethyl)-9-azatricyclo[5.3.1.02,6]undec-3-ene (Preparation 35, 6.7 g, 28.0 mmol), N-methylmorpholine N-oxide (3.45 g, 29.45 mmol) and osmium tetroxide (2.5 wt % in 2-methyl-2-propanol, 2 □l) in acetone (50 ml) was stirred for 18 h. Florisil and aqueous sodium hydrogensulfite (4 ml) were added and the reaction mixture was stirred for 30 min and filtered. Methanol (50 ml) was added and the reaction mixture was concentrated to give an oil which was purified by flash chromatography eluting with ethyl acetate:hexane (50:50) to give an oil (6.2 g, 80%) which crystallises upon standing.

Aufarbeitung

  1. filtrationfiltered
  2. additionMethanol (50 ml) was added
  3. concentrationthe reaction mixture was concentrated
  4. customto give an oil which
  5. customwas purified by flash chromatography
  6. washeluting with ethyl acetate:hexane (50:50)

Quellen und Nachweise

ORD-Eintrag
ord-77aa9fbaf587432baea86712004ca9a5
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07494992B2

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