Water → HCID 19823817, compound

HRID 728287Notes

Reaction equation

HRID 728287 reaction equation
[CH3:1][N:2]([CH:4]([C:9]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:12][CH2:11][CH2:10]1)[CH2:5][CH2:6][CH:7]=[CH2:8])[CH3:3].S(=O)(O)[O-:22].[Na+].[OH2:26]>N1C=CC=CC=1.[Os](=O)(=O)(=O)=O>[Cl:20][C:15]1[CH:14]=[C:13]([C:9]2([CH:4]([N:2]([CH3:3])[CH3:1])[CH2:5][CH2:6][CH:7]([OH:22])[CH2:8][OH:26])[CH2:12][CH2:11][CH2:10]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

6

Reactant 3

HCID 962WaterHCID 19823832HCID 19823832, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19823817HCID 19823817, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 1049PyridineSolvent3×

Procedure

A solution of osmium tetroxide (2 g) in pyridine (10 ml) was added with stirring to a solution of N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]pent-4-enylamine (2.43 g) in pyridine (20 ml). The mixture was allowed to stand for one and three quarter hours and was then added to a mixture of pyridine (40 ml) and a solution of sodium bisulphite (3.6 g) in water (60 ml). The resulting aqueous layer was extracted with dichloromethane and the extracts washed, dried and evaporated in vacuo to give a residue which was purified by flash chromatography using ether as eluant to give 5-[1-(3,4-dichlorophenyl)cyclobutyl]-5-dimethylaminopentane-1,2-diol the boiling point of which was not determined.

Workup

  1. waitto stand for one and three quarter hours
  2. extractionThe resulting aqueous layer was extracted with dichloromethane
  3. washthe extracts washed
  4. customdried
  5. customevaporated in vacuo
  6. customto give a residue which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-e7d37ad0820941dfa1699100a7a09b54
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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