Benzylethanolamine → 2-[Benzyl({3-chloro-5-[methyl(1-methylpropyl)amino]pyrazin-2-yl}methyl)amino]ethanol
Reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:17]([CH:28]=O)=[N:18][CH:19]=[C:20]([N:22]([CH3:27])[CH:23]([CH3:26])[CH2:24][CH3:25])[N:21]=1.[CH2:30]([NH:37][CH2:38][CH2:39][OH:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:30]([N:37]([CH2:28][C:17]1[C:16]([Cl:15])=[N:21][C:20]([N:22]([CH3:27])[CH:23]([CH3:26])[CH2:24][CH3:25])=[CH:19][N:18]=1)[CH2:38][CH2:39][OH:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium triacetoxyborohydride (2.0 g) was added to a solution of 3-chloro-5-[methyl(1-methylpropyl)amino]pyrazine-2-carbaldehyde (1.43 g), N-benzylethanolamine (1.14 g) and acetic acid (1.08 mL) in acetonitrile (10 mL), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was basified with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 20→80% ethyl acetate/hexane) to give the title compound (2.07 g, 91%) as a pale-yellow oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- extractionThe aqueous layer was extracted again with ethyl acetate
- washThe combined organic layer was washed with water and saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (solvent gradient: 20→80% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-fe84721c44a742bb9df27fe1216994f9
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115139B2
Reaction notes
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