Triethylamine → HCID 86663487, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH2:14][CH2:15][OH:16])[O:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:24][C:25]([F:40])([F:39])[C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1)[C:29](Cl)=[O:30]>C(#N)C.O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:24][C:25]([F:39])([F:40])[C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([C:35]([F:38])([F:36])[F:37])[CH:34]=1)[C:29]([N:10]1[CH2:11][CH2:12][O:13][C@:8]([CH2:14][CH2:15][OH:16])([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9]1)=[O:30]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Procedure
2-[(2R)-2-(4-Fluorophenyl)morpholin-2-yl]ethanol (1.76 g, 7.82 mmol) and triethylamine (1.32 mL, 9.38 mmol) were dissolved in a mixed solvent of acetonitrile (18 mL) and water (0.9 mL). A solution of 3,5-bis(trifluoromethyl)benzoyl chloride (1.48 mL, 8.21 mmol) in toluene (8.2 mL) was added dropwise with stirring under ice cooling, and then the mixture was further stirred under the same conditions for 5 minutes. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude 2-[(2R)-4-[3,5-bis(trifluoromethyl)benzoyl]-2-(4-fluorophenyl)morpholin-2-yl]ethanol (3.74 g) as a colorless oily substance.
Workup
- stirringthe mixture was further stirred under the same conditions for 5 minutes
- washthe organic layer was washed with water and saturated sodium chloride solution
- dry with materialThe organic layer was dried with anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-613195899aa041b29218214678c2253e
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476253B2
Reaction notes
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