Hydrochloric Acid → Ethyl(1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate
Reaction equation
[F:1][C:2]1([C:9]([OH:11])=[O:10])[CH:7]2[CH:3]1[CH2:4][CH2:5][C:6]2=[O:8].C(=O)([O-])O.[Na+].[CH2:17](I)[CH3:18].Cl>CN(C)C=O>[F:1][C:2]1([C:9]([O:11][CH2:17][CH3:18])=[O:10])[CH:7]2[CH:3]1[CH2:4][CH2:5][C:6]2=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
(1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid in an amount of 1.0 g was dissolved in 5.0 mL of N,N-dimethylformamide, and 0.58 g of sodium hydrogencarbonate and 1.5 mL of ethyl iodide were added thereto. The mixture was stirred overnight at 50° C. The reaction mixture was poured into 1M hydrochloric acid, followed by extractions with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1), thereby yielding 1.1 g of (1RS,5RS,6RS)ethyl 6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate.
Workup
- extractionfollowed by extractions with ethyl acetate three times
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationAfter the desiccant was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by column chromatography (silica gel: Wako gel C200 (produced by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=8:1)
Sources & evidence
- ORD record
- ord-9ad01512c32049beb83c03d2a4793c32
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825375B2
Reaction notes
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