Sodium Iodide → N-{[2-(2,2-Difluorocyclopropyl)acetoxy]acetyl}pyrrolidine
Reaction equation
[F:1][C:2]1([F:9])[CH2:4][CH:3]1[CH2:5][C:6]([OH:8])=[O:7].Br[CH2:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].[I-].[Na+].C(N(CC)CC)C>CN(C)C=O.O>[F:1][C:2]1([F:9])[CH2:4][CH:3]1[CH2:5][C:6]([O:8][CH2:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2.72 g (0.02 mol) 2,2-difluorocyclopropyl-acetic acid and 3.84 g (0.02 mol) N-(bromoacetyl)-pyrrolidine in 10 ml dimethylformamide was treated, at room temperature, with 0.3 g sodium iodide and 2.8 ml (0.02 ml) triethylamine and the mixture stirred at room temperature for 10 hours. It was then poured into water and extracted three times with ethyl acetate. The combined ethyl acetate phases were washed with first with aqueous 2% sodium hydrogen carbonate and then with water, dried over magnesium sulphate and concentrated. The crude product was purified by silica gel column chromatography using hexane/ethyl acetate (1:1) as eluent. A sample was analysed by thin layer chromatography using hexane/ethyl acetate (1:1) as eluent (Rf :0.18). 3.3 g (66% of theory) of product was obtained.
Workup
- extractionextracted three times with ethyl acetate
- washThe combined ethyl acetate phases were washed with first with aqueous 2% sodium hydrogen carbonate
- dry with materialwith water, dried over magnesium sulphate
- concentrationconcentrated
- customThe crude product was purified by silica gel column chromatography
- custom3.3 g (66% of theory) of product was obtained
Sources & evidence
- ORD record
- ord-c2d049c7b50e48e9b5c2d6bb853ed879
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05071869
Reaction notes
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