Diisopropylethylamine → 1,1,1-trifluoro-3-[4-(4-nitrophenyl)-3,6-dihydropyridin-1(2H)-yl]propan-2-ol

HRID 1520036Notes

Reaction equation

HRID 1520036 reaction equation
[O:1]1[CH:3]([C:4]([F:7])([F:6])[F:5])[CH2:2]1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9].CCN(C(C)C)C(C)C>CN(C=O)C.O.CCOC(C)=O>[F:5][C:4]([F:7])([F:6])[CH:3]([OH:1])[CH2:2][N:20]1[CH2:19][CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 5207692-(Trifluoromethyl)oxiraneHCID 220487834-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 679811441,1,1-trifluoro-3-[4-(4-nitrophenyl)-3,6-dihydropyridin-1(2H)-yl]propan-2-olYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

1,2-Epoxy-3,3,3-trifluoropropane, tech., 85% (2.32 g; 17.63 mmol; 1.20 eq.) was added to a suspension of 4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine (3.0 g; 14.7 mmol; 1.0 eq.) in DMF (60 mL) and DIEA (2.5 mL, 14.7 mmol, 1 eq.). The reaction mixture was heated at 45° C. for 4 h. It was then allowed to cool down to RT and diluted with water (50 mL) and EtOAc (100 mL). Organic layer was washed with a saturated solution of NH4Cl (2×50 mL) and water, dried over magnesium sulfate, filtered and concentrated to give the expected compound as an orange solid (3.6 g, 77%). UPLC/MS: (MS+) 317.3, (MS−) 315.3.

Workup

  1. temperatureto cool down to RT
  2. washOrganic layer was washed with a saturated solution of NH4Cl (2×50 mL) and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-868a152749074e2a923686a37a3c4782
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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