Sodium Sulfite → (2S,4S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate
Reaction equation
[I:1][C:2]1[N:3]=[C:4]([C@@H:8]2[CH2:12][C@H:11]([CH3:13])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:5][C:6]=1I.S([O-])([O-])=O.[Na+].[Na+]>C(O)C.O>[I:1][C:2]1[NH:3][C:4]([C@@H:8]2[CH2:12][C@H:11]([CH3:13])[CH2:10][N:9]2[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[N:5][CH:6]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A solution of (2S,4S)-tert-butyl 2-(4,5-diiodo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate (2.25 g, 4.4 mmol) in 18 mL ethanol and 18 mL water was treated with sodium sulfite (5.59 g, 44.4 mmol) and heated at 90° C. overnight. The mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with more ethyl acetate and the combined organic phase was washed with brine, dried over sodium sulphate, filtered, concentrated, and purified by silica gel chromatography to give 766 mg (2S,4S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate.
Workup
- customThe mixture was partitioned between ethyl acetate and water
- extractionThe aqueous phase was extracted with more ethyl acetate
- washthe combined organic phase was washed with brine
- dry with materialdried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-706b6cb520664e3daaf27e64f272eb10
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156823B2
Reaction notes
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