Ethanolamine → 2-{[(3,4,5-Trifluorophenyl)methyl]amino}ethan-1-ol
Reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:25])[C:23]=1[F:24])[CH:19]=O.[CH2:26]([CH2:28][NH2:29])[OH:27].[OH-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.C(O)(=O)C>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:25])[C:23]=1[F:24])[CH2:19][NH:29][CH2:28][CH2:26][OH:27]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium triacetoxyborohydride (14.1 g) was added to a solution of 3,4,5-trifluorobenzaldehyde (5.0 mL), ethanolamine (3.52 g), and acetic acid (10.1 mL) in THF (100 mL) under ice-cooling, and the reaction solution was stirred at room temperature for four hours and 30 minutes. Ice water was added to the reaction solution. The reaction solution was adjusted to pH 7 to 8 by a 5 N sodium hydroxide solution and saturated sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the mother liquor was concentrated under reduced pressure. The residue was purified by column chromatography using a silica gel (chloroform:methanol=1:100 to 1:5) to obtain 6.91 g of the title compound.
Workup
- temperaturecooling
- extractionfollowed by extraction with chloroform
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationthe mother liquor was concentrated under reduced pressure
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-e395839f3035407d94d1c44fdfb15ad0
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618960B2
Reaction notes
Loading…