Acetic Acid → Methyl (1S,3S,4S,6R,7S)-6-acetyloxy-7-iodo-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
Reaction equation
[C:1]1([C@H:7]([N:9]2[C@H:14]([C:15]([O:17][CH3:18])=[O:16])[C@@H:13]3[CH2:19][C@H:10]2[CH:11]=[CH:12]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:20]N1C(C)(C)C(=O)N(I)C1=O.[C:31]([OH:34])(=[O:33])[CH3:32]>>[C:31]([O:34][C@H:11]1[C@H:10]2[C@@H:19]([I:20])[C@H:13]([C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:9]2[C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH2:12]1)(=[O:33])[CH3:32]Participants
4
Reactant 3
Product 1
Procedure
To a solution of methyl (1S,3S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate obtained in Example 42-2 (1.0 g) in acetic acid (9 mL), was added portionwise 1,3-diiodo-5,5-dimethylhydantoin (782 mg). The mixture was stirred at room temperature for 30 minutes. The solution was concentrated under reduced pressure. The resulting mixture was diluted with ethyl acetate, and washed successively with sodium hydrogencarbonate solution, sodium thiosulfate solution, sodium hydrogen carbonate solution and brine. The organic layer was dried over MgSO4 and evaporated in vacuo to give the target compound as a solid (1.74 g).
Workup
- concentrationThe solution was concentrated under reduced pressure
- additionThe resulting mixture was diluted with ethyl acetate
- washwashed successively with sodium hydrogencarbonate solution, sodium thiosulfate solution, sodium hydrogen carbonate solution and brine
- dry with materialThe organic layer was dried over MgSO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-87e862f1fe30413f971d672b54912059
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186731B2
Reaction notes
Loading…