Acetic Acid → 2-benzyl-3-iodo-6-[(3R,4S)-3-acetoxy-4-methoxypyrrolidin-1-yl]pyridine

HRID 2216343Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([OH:10])(=[O:9])[CH3:8].[CH2:11]([C:18]1[C:23]([I:24])=[CH:22][CH:21]=[C:20]([N:25]2[CH2:29][C@H:28]([O:30][CH3:31])[C@@H:27](OS(C3C=CC=C([N+]([O-])=O)C=3)(=O)=O)[CH2:26]2)[N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O>[CH2:11]([C:18]1[C:23]([I:24])=[CH:22][CH:21]=[C:20]([N:25]2[CH2:29][C@H:28]([O:30][CH3:31])[C@H:27]([O:9][C:7](=[O:10])[CH3:8])[CH2:26]2)[N:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 7.9 g of cesium carbonate and 15 ml of dimethyl sulfoxide was added 4.2 ml of acetic acid. After foaming ceased, a mixture of 14.4 g of 2-benzyl-3-iodo-6-[(3S,4S)-3-(3-nitrobenzenesulfonyl)oxy-4-methoxypyrrolidin-1-yl]pyridine and 35 ml of dimethyl sulfoxide was added and the resultant mixture was heated under stirring under nitrogen atmosphere in an oil bath at 70° C. for 6 hours. After the reaction mixture was cooled, it was extracted with ethyl acetate-water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (10–15% ethyl acetate/hexane), to give 7.5 g of the title compound.

Workup

additionwas added
temperatureAfter the reaction mixture was cooled
extractionit was extracted with ethyl acetate-water
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (10–15% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d0d953a32d504cac83ce6b29c928132a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112593B2

Reaction notes

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