4-Methoxybenzaldehyde → HCID 68703214, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:19])[NH:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[CH2:7][NH2:8])[CH3:2].[CH:20](=O)[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:3][C:4](=[O:19])[NH:5][C@@H:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=1)[CH2:7][NH:8][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Crude (S)-[2-amino-1-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid ethyl ester from above is dissolved in anhydrous EtOH (100 mL). p-Anisaldehyde (2.07 g, 15.2 mmol) is added into the solution and stirred at room temperature for 5 h before the addition of NaBH4 (0.82 g, 21.8 mmol) at 0° C. The mixture is then warmed up to room temperature and stirred for 14 hr. After the solvent is removed under vacuum, the residue is treated with saturated NH4Cl aqueous solution (50 mL) and extracted with EtOAc (3×150 mL). The combined organic layer is washed with brine and dried (MgSO4). After removing the drying agent, the solution is concentrated to provide the crude (S)-[2-(4-methoxy-benzylamino)-1-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid ethyl ester as colorless oil (˜6.0 g) which is used directly for next step.
Workup
- customAfter the solvent is removed under vacuum
- additionthe residue is treated with saturated NH4Cl aqueous solution (50 mL)
- extractionextracted with EtOAc (3×150 mL)
- washThe combined organic layer is washed with brine
- dry with materialdried (MgSO4)
- customAfter removing the drying agent
- concentrationthe solution is concentrated
Sources & evidence
- ORD record
- ord-d2ec52d72668465eb4aa2f8011748161
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431607B2
Reaction notes
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