Reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[NH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].[BH4-].[Na+]>CO.CCOC(C)=O.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([NH2:9])=[C:11]([N+:18]([O-:20])=[O:19])[CH:12]=2)[CH2:5][CH2:4]1)[CH3:2]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirred solution of 1-ethyl-piperazine (1.37 g, 12 mmol) in MeOH (30 mL) was added Ti(OiPr)4 (1.73 g, 6 mmol). Then the solution was stirred at room temperature for 15 min. Then 4-amino-3-nitro-benzaldehyde (Procedure 2F, steps a-b, 1.5 g, 9 mmol) in MeOH (10 mL) was added and the solution was stirred at room temperature overnight. Then NaBH4 (380 mg, 10 mmol) was added and the solution was stirred at room temperature for 1 hour. The solution was diluted with EtOAc and filtered. The filtrate was washed with water and brine, dried over anhydrous Na2SO4. Concentration gave product, which was purified by flash chromatography on silica to obtain the title compound (800 mg, yield: 34%). MS (ESI): 265 [M+H]+
Workup
- stirringthe solution was stirred at room temperature overnight
- stirringthe solution was stirred at room temperature for 1 hour
- filtrationfiltered
- washThe filtrate was washed with water and brine
- dry with materialdried over anhydrous Na2SO4
- concentrationConcentration
- customgave product, which
- customwas purified by flash chromatography on silica
Sources & evidence
- ORD record
- ord-09b9e11eaef04abeafbfb647896bb2e2
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434697B2
Linked notes
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