Hydrochloric Acid → (2'-Aminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[C:24]#[N:25])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[BH4-].[Na+].Cl>CO.C1COCC1.O.O.O.O.O.O.[Co](Cl)Cl>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=2[CH2:24][NH2:25])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of (2′-cyano-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.545 g, 1.5 mmol) and cobalt(II) chloride hexahydrate (0.71 g, 3.0 mmol) in MeOH (60 mL) and THF (24 mL) was added sodium borohydride (0.58 g, 15.3 mmol), and the reaction was stirred at room temperature for 2 hours. 2N Aqueous HCl (67 mL) was added, and the mixture was concentrated. 2N Aqueous NH4OH was added until the solution was basic, and the mixture was extracted twice with CH2Cl2. The combined organic layers were washed three times with H2O, dried over Na2SO4, filtered, and concentrated to give the title compound.
Workup
- concentrationthe mixture was concentrated
- addition2N Aqueous NH4OH was added until the solution
- extractionthe mixture was extracted twice with CH2Cl2
- washThe combined organic layers were washed three times with H2O
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-99db4b4319b64de18228dd1e80823dc5
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067445B2
Reaction notes
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