Sodium hydride → (S)-methyl 2-(4-benzyl-2-ethylpiperazine-1-yl)benzoxazole-4-carboxylate
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[O:20][C:21]2[C:22](=[C:24]([C:28]([O:30][CH3:31])=[O:29])[CH:25]=[CH:26][CH:27]=2)[N:23]=1>COCCOC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:19]2[O:20][C:21]3[C:22](=[C:24]([C:28]([O:30][CH3:31])=[O:29])[CH:25]=[CH:26][CH:27]=3)[N:23]=2)[C@@H:10]([CH2:14][CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (S)-1-benzyl-3-ethylpiperazine (650 mg, 3.22 mmol) in DME (10 mL) at room temperature, was added NaH (60% suspension in mineral oil, 144 mg, 3.50 mmol) and the mixture was stirred for 45 min. Methyl 2-chlorobenzoxazole-4-carboxylate (510 mg, 2.42 mmol) was added to the reaction mixture and the reaction was stirred at room temperature for 17 h. The reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL) was added, and solvent removed under reduced pressure. The mixture was purified by column chromatography (silica gel, 0 to 80% EtOAc in hexanes) to afford (S)-methyl 2-(4-benzyl-2-ethylpiperazine-1-yl)benzoxazole-4-carboxylate (0.87 g, 71%) as an oily solid. 1H NMR and MS consistent.
Workup
- stirringthe reaction was stirred at room temperature for 17 h
- customThe reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL)
- additionwas added
- customsolvent removed under reduced pressure
- customThe mixture was purified by column chromatography (silica gel, 0 to 80% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-2b25d8c611784ee59838fba0d71c1861
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863271B2
Reaction notes
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