1,4-Dibromobenzene → HCID 57446955, compound
Reaction equation
C([Li])CCC.C1CCCCC1.Br[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1.[CH2:20]([C@H:23]1[CH2:27][O:26][CH:25]([C:28]([F:31])([F:30])[F:29])[NH:24]1)[CH2:21][CH3:22]>CCOCC.O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([CH:25]([NH:24][C@@H:23]([CH2:20][CH2:21][CH3:22])[CH2:27][OH:26])[C:28]([F:30])([F:29])[F:31])=[CH:14][CH:15]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Butyllithium (41 mL of a 2.0M cyclohexane solution) was added at −30° C. to a solution of 1,4-dibromobenzene (19.3 g, 81.89 mmol) in ether (250 mL) over 10 minutes. After 1 hour, a solution of (4S)-4-propyl-2-trifluoromethyloxazolidine (3.00 g, 16.38 mmol) was added in ether (50 mL) over 30 minutes via an addition funnel. After 90 minutes of stirring, water (100 mL) was added. The organic phase was washed with brine (100 mL), dried over MgSO4, filtered, and evaporated to dryness. The residue was purified on a plug of silica gel (10-30% ethyl acetate/hexane elution). An approximately 2:1 mixture of diastomers of (2S)-2-[1-(4-bromophenyl)-2,2,2-trifluoroethylamino]-pentan-1-ol at the CF3 residue was observed based on the norvaline methyl triplet at 0.98 ppm (1H NMR).
Workup
- washThe organic phase was washed with brine (100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified on a plug of silica gel (10-30% ethyl acetate/hexane elution)
- additionAn approximately 2:1 mixture of diastomers of (2S)-2-[1-(4-bromophenyl)-2,2,2-trifluoroethylamino]-pentan-1-ol at the CF3 residue
Sources & evidence
- ORD record
- ord-ce1a741ee4664d5d93cbf361d34aaac7
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973037B2
Reaction notes
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