Borane;tetrahydrofuran → 3-[2-(3-Isopropylphenylamino)ethylamino]benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=O)[CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:15]=2)[CH:5]=1.B.C1COCC1>>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:21])[CH3:22])[CH:15]=2)[CH:5]=1Participants
Procedure
3-[2-(3-Isopropylphenylamino)acetylamino]benzoic acid methyl ester (3.26 g, 10.0 mmol) prepared above was treated with BH3.THF (1.0 M, 40.0 mL, 40.0 mmol) at room temperature for 24 h. The excess borane was destroyed by the addition of HCl (6 M, 10 mL). THF was removed in vacuum and the residue was diluted with water and basified. The organics were separated and the aqueous phase was extracted with dichloromethane. The organics were combined and washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The crude product obtained after the removal of the solvent in vacuum was chromatographed (silica gel, dichloromethane:ethyl acetate, 9.5:0.5) to furnish 3-[2-(3-isopropylphenylamino)ethylamino]benzoic acid methyl ester as a colorless oil (2.28 g, 73.1%). MS (ES+) m/z: 313.
Workup
- customThe excess borane was destroyed by the addition of HCl (6 M, 10 mL)
- customTHF was removed in vacuum
- additionthe residue was diluted with water
- customThe organics were separated
- extractionthe aqueous phase was extracted with dichloromethane
- washwashed with water and brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe crude product obtained
- customafter the removal of the solvent in vacuum
- customwas chromatographed (silica gel, dichloromethane:ethyl acetate, 9.5:0.5)
Sources & evidence
- ORD record
- ord-f42ccfd0b94a41a2ba3b969053291fec
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902241B2
Reaction notes
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