1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86667307, compound

HRID 1427514Notes

Reaction equation

HRID 1427514 reaction equation
[N+:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([O-:3])=[O:2].[CH2:21]1[CH2:31][CH2:30]N2C(=NCCC2)C[CH2:22]1.C1(C=O)CC1>CN(C=O)C.O>[CH:21]1(/[CH:22]=[C:4](/[C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)\[N+:1]([O-:3])=[O:2])[CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123114CyclopropanecarboxaldehydeHCID 86667306HCID 86667306, compound

Product 1

HCID 86667307HCID 86667307, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 4-(nitromethyl)-4′-(trifluoromethyl)biphenyl (200 mg, 0.711 mmol) and DBU (54.4 mg, 0.355 mmol) in DMF (3 ml) was added cyclopropanecarbaldehyde (99.7 mg, 1.42 mmol). The reaction mixture was stirred at room temperature overnight. The resulting mixture was diluted with water and extracted with ethyl acetate (10 mL*3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by preparative TLC to give impure (Z)-4-(2-cyclopropyl-1-nitrovinyl)-4′-(trifluoromethyl)biphenyl (110 mg) as a colorless solid. To a solution of the impure (Z)-4-(2-cyclopropyl-1-nitrovinyl)-4′-(trifluoromethyl)biphenyl (55 mg, 0.16 mmol) in THF (3 mL) was added Raney nickel. The reaction mixture was stirred at room temperature under an atmosphere of hydrogen (40 psi) overnight. The reaction mixture was purified by preparative TLC to give 2-cyclopropyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)ethanamine (20 mg) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.62-7.60 (m, 4H), 7.49 (d, J=8.0 Hz, 2H), 7.39 (d, J=8.0 Hz, 2H), 4.04-4.08 (m, 1H), 1.70-1.56 (m, 1H), 1.54-1.49 (m, 1H), 0.65-0.50 (m, 1H), 0.45-0.30 (m, 2H), 0.15-0.00 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (10 mL*3)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-fe2645d1a8ff42079a0cc998405b8061
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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