Toluene → {4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanol

HRID 1691529Notes

Reaction equation

HRID 1691529 reaction equation
[CH3:1][CH:2]([CH3:32])[CH2:3][CH2:4][N:5]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26](OC)=[O:27])=[CH:24][CH:23]=1)[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:10]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][CH:2]([CH3:32])[CH2:3][CH2:4][N:5]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[CH:30][CH:31]=1)[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[N:10]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 23157327Methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate

Product 1

HCID 23157500{4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanolYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate (1.34 g, 2.90 mmol) in tetrahydrofuran (10 mL) was added dropwise a toluene solution (1.0 M, 6.38 mL, 6.38 mmol) of diisobutylaluminum hydride under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, sodium sulfate 10 hydrate was added, and the mixture was further stirred for 1 hr. The insoluble material was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-60:40) to give the title compound (0.950 g, yield 75%) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  3. filtrationThe insoluble material was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-60:40)

Sources & evidence

ORD record
ord-293f5b6a7ffd49cb90fe13ce586a1a47
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

Loading…