Reaction equation
[Li][CH3:2].[Li+].[Br-].C[Si](Cl)(C)C.[CH2:10]([O:12][C:13](=[O:30])/[CH:14]=[CH:15]/[C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH3:11].[Cl-].[NH4+].[OH-].[NH4+]>C1COCC1.[Cu]I>[CH2:10]([O:12][C:13](=[O:30])[CH2:14][C@H:15]([C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH3:2])[CH3:11]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To CuI (3.36 g, 17.64 mmol) in THF (15 mL) was added at −78° C. MeLi.LiBr (1.5M in ether, 23.5 mL, 35.28 mmol), and the resulting mixture was stirred at −78° C. for 15 min. TMSCl (1.52 mL, 17.64 mmol) and Me2CuLi (generated above) were added in sequence at −78° C. to (S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate (0.88 g, 2.94 mmol), and the resulting mixture was slowly warmed up to rt. Ammonium chloride-ammonium hydroxide buffer (pH ˜8) was added to the reaction mixture. The mixture was extracted with ether, washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography (silica gel, 2:8=ethyl acetate:hexanes) gave (S)-tert-butyl 4-((R)-4-ethoxy-4-oxobutan-2-yl)-2,2-dimethyloxazolidine-3-carboxylate as a clear oil.
Workup
- extractionThe mixture was extracted with ether
- washwashed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7d8d6197b34c466986f01dabcd3cfa73
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312218B2
Linked notes
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