Sodium Bicarbonate → 1-[(2-Methylquinolin-5-yl)amino]-4,4-dimethyl-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1869355Notes

Reaction equation

HRID 1869355 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([O-])(O)=O.[Na+]>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

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 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 is mixed with saturated NaHCO3 and heated to room temperature. The phases are 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 phases are 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-84b9ecc1dea2467d8bab6f6382b36d9d
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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