3,3,3-Trifluoropropanal → 4-(4-Nitrophenyl)-1-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyridine
Reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:25][CH2:26][NH:27][CH2:28][CH:29]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16].CCN(C(C)C)C(C)C.[F:39][C:40]([F:45])([F:44])[CH2:41][CH:42]=O>ClCCCl>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH2:29][CH2:28][N:27]([CH2:42][CH2:41][C:40]([F:45])([F:44])[F:39])[CH2:26][CH:25]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Sodium triacetoxyborohydride (6.2 g, 29.4 mmol, 2 eq.) was added to a solution of 4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine (3.0 g; 14.7 mmol; 1.0 eq.), DIEA (2.5 mL; 14.7 mmol; 1.0 eq.) and 3,3,3-Trifluoropropanal (2.4 mL; 29.4 mmol; 2.0 eq.) in DCE (60 mL). The reaction mixture was heated at 50° C. for 2 h and quenched by addition of a saturated solution of NH4Cl (50 mL). The phases were separated and organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated to give a brown crude. Purification by flash chromatography on silica (EtOAc:heptane) afforded the title compound as a yellow solid (2.0 g, 45%). UPLC/MS: (MS+) 301.4.
Workup
- customquenched by addition of a saturated solution of NH4Cl (50 mL)
- customThe phases were separated
- washorganic phase was washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give a brown crude
- customPurification by flash chromatography on silica (EtOAc:heptane)
Sources & evidence
- ORD record
- ord-85a648b812dc4c6cbac6b082de4a6cb1
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073892B2
Reaction notes
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