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

HRID 1727190Notes

Reaction equation

HRID 1727190 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-77aa9fbaf587432baea86712004ca9a5
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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