1,1,1-Trifluoro-4-phenyl-2-[(2-methylquinolin-5-yl)iminomethyl]-4-methylpentan-2-ol → 1-[(2-Methylquinolin-5-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1444440Notes

Reaction equation

HRID 1444440 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]([CH:15]=[N:16][C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH3:27])=[N:22]2)([OH:14])[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH3:6]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:27][C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[CH:26][C:17]=2[NH:16][CH:15]2[C:9]3[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]([CH3:6])([CH3:7])[CH2:4][C:3]2([C:2]([F:1])([F:28])[F:29])[OH:14])[N:22]=1

Participants

4

Reactant 1

HCID 179891651,1,1-Trifluoro-4-phenyl-2-[(2-methylquinolin-5-yl)iminomethyl]-4-methylpentan-2-ol

Product 1

HCID 686823591-[(2-Methylquinolin-5-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-2-olYield 84.7%

Reagents, catalysts & solvents 2

HCID 57473882titanium tetrachloride CH2Cl2CatalystHCID 6344DichloromethaneSolvent

Procedure

5.1 ml of a 1 M titanium tetrachloride-CH2Cl2 solution is added in drops to a solution of 111 mg of 1,1,1-trifluoro-4-phenyl-2-[(2-methylquinolin-5-yl)iminomethyl]-4-methylpentan-2-ol in 84 ml of CH2Cl2 at −78° C. After 1 hour at −78° C., the batch separated, the aqueous phase is extracted with CH2Cl2, the combined organic phases are dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with cyclohexane-ethyl acetate yields 94 mg of product.

Workup

  1. customthe batch separated
  2. extractionthe aqueous phase is extracted with CH2Cl2
  3. dry with materialthe combined organic phases are dried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-042a0cc7c672411e8405dd4e8ad8f2c3
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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