Water → 2-Benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine
Reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][CH:17]=[CH:16][CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC=C(N2CCCC2)N=1)C1C=CC=CC=1.C[N+]1([O-])CC[O:41]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH2:52]>[Os](=O)(=O)(=O)=O.CC(C)=O.CC(O)(C)C>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@H:17]([OH:52])[C@H:16]([OH:41])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
2.3 ml of a 2-methyl-2-propanol solution containing 2.5% osmium tetraoxide was added dropwise little by little into a mixture of 11.8 g of a mixture of 2-benzyl-6-(3-pyrroline-1-yl)pyridine and 2-benzyl-6-(pyrrolidine-1-yl)pyridine, 23.5 g of aqueous 50% N-methylmorpholine-N-oxide solution, 50 ml of acetone and 10 ml of water in an ice bath. After stirring for 2 hours in an ice bath, it was further stirred at room temperature overnight. A aqueous sodium thiosulfate solution was added to the reaction solution, followed by stirring at room temperature for 30 minutes. Then, the mixture was extracted with ethyl acetate, and the organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to silica gel column chromatography and eluted with hexane/ethyl acetate (5:1) and then with ethyl acetate, to give 4.2 g of the target compound.
Workup
- additionwas added dropwise little by
- stirringit was further stirred at room temperature overnight
- stirringby stirring at room temperature for 30 minutes
- extractionThen, the mixture was extracted with ethyl acetate
- washthe organic phase was washed with water and brine
- customthe solvent was removed
- washeluted with hexane/ethyl acetate (5:1)
Sources & evidence
- ORD record
- ord-a30c8827e3c549c9997591e24a74bbcf
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06599917B1
Reaction notes
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