反应 #595181

ord-3b77d3dbc0854d6ebb249426aaa7b994

反应方程式

O.O.O.O.O.O.O.O.O.O.O=S(=O)([O-])[O-].[Na+].[Na+]
sodium sulfate decahydrate
COC(=O)c1ccc(CN(CCC(C)C)c2nc(-c3ccc(C(F)(F)F)cc3)cs2)cc1
methyl 4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzoate
CC(C)[CH2][Al+][CH2]C(C)C.Cc1ccccc1.[H-]
diisobutylaluminum hydride toluene
CC(C)CCN(Cc1ccc(CO)cc1)c1nc(-c2ccc(C(F)(F)F)cc2)cs1
title compound
收率 75.4%
CC(C)CCN(Cc1ccc(CO)cc1)c1nc(-c2ccc(C(F)(F)F)cc2)cs1
{4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanol
收率 75.4%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度cooling
  2. 2
    workup.STIRRINGthe mixture was further stirred at room temperature for 1 hr
  3. 3
    过滤The insoluble material was filtered off
  4. 4
    浓缩the filtrate was concentrated
  5. 5
    其他The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90-60/40)

实验过程

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 1.0 M diisobutylaluminum hydride toluene solution (6.38 mL, 6.38 mmol) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, sodium sulfate decahydrate was added and the mixture was further stirred at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90-60/40) to give the title compound (950 mg, yield 75%) as a colorless oil.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07786165B2uspto-grants-2010_08