Ammonium Chloride → HCID 59281211, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])CCC.[CH2:14]([O:21][CH2:22][C@@H:23]1[O:31][CH2:30][C:26]2=[N:27][O:28][CH2:29][C@@H:25]2[CH2:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1COCC1>[CH2:14]([O:21][CH2:22][C@@H:23]1[O:31][CH2:30][C@:26]2([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[F:8])[NH:27][O:28][CH2:29][C@@H:25]2[CH2:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
Toluene (100 ml) and THF (10 ml) were added to 2-bromofluorobenzene (3.11 g). The reaction solution was cooled to −78° C., and n-butyllithium (2.63 M, 6.15 ml) was added dropwise. After stirring at the same temperature for one hour, a mixed solution of (3aR,5R)-5-benzyloxymethyl-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole (2.00 g) in toluene (20 ml) and THF (2 ml) and a boron trifluoride-diethyl ether complex (2.03 ml) were added dropwise at the same time. After stirring at the same temperature for two hours, an ammonium chloride solution was added to the reaction solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (2.29 g).
Workup
- stirringAfter stirring at the same temperature for two hours
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-64b84a5cf96643b0843083782e255e58
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198269B2
Reaction notes
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