Trimethylamine oxide dihydrate → 6,7,8,9-Tetrahydro-5H-6,9-methanocyclohepta[b]pyridine-7,8-diol

HRID 1727184Notes

Reaction equation

HRID 1727184 reaction equation
[CH:1]12[CH2:12][CH:9]([CH:10]=[CH:11]1)[CH2:8][C:7]1[C:2]2=[N:3][CH:4]=[CH:5][CH:6]=1.[OH2:13].[OH2:14].C[N+]([O-])(C)C>ClCCl.[Os](=O)(=O)(=O)=O>[CH:1]12[CH2:12][CH:9]([CH:10]([OH:14])[CH:11]1[OH:13])[CH2:8][C:7]1[C:2]2=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 198430Trimethylamine oxide dihydrateHCID 688081066,9-Dihydro-5H-6,9-methanocyclohepta[b]pyridine

Product 1

HCID 688083706,7,8,9-Tetrahydro-5H-6,9-methanocyclohepta[b]pyridine-7,8-diolYield 100%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-azatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraene (Preparation 25, 0.96 g, 6.11 mmol), trimethylamine N-oxide dihydrate (0.75 g, 6.73 mmol) and osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, 2 □l) in dichloromethane (15 ml) were stirred for 18 h. A further portion of osmium tetroxide (2.5 wt % solution in 2-methyl-2-propanol, ca. 1 □l) was added and the reaction mixture was stirred for a further 18 h. The reaction mixture was subjected to chromatography eluting with hexane and then ethyl acetate to give the title compound as a solid (1.16 g, 100%).

Workup

  1. stirringthe reaction mixture was stirred for a further 18 h
  2. washeluting with hexane

Sources & evidence

ORD record
ord-4394d0ebc9d9429dbc4149a42a102f5b
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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