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3,3,3-Trifluoropropanal → 4-(4-Nitrophenyl)-1-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyridine

HRID 1520034
Notes
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Reaction equation

HRID 1520034 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 680283,3,3-TrifluoropropanalHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 220487834-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 679846324-(4-Nitrophenyl)-1-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyridineYield 45.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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

  1. customquenched by addition of a saturated solution of NH4Cl (50 mL)
  2. customThe phases were separated
  3. washorganic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown crude
  8. customPurification by flash chromatography on silica (EtOAc:heptane)

Sources & evidence

ORD record
ord-85a648b812dc4c6cbac6b082de4a6cb1
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073892B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes