Citric Acid → 4-[2-(t-Butyldimethyl silanyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carboxaldehyde

HRID 420606노트

반응식

HRID 420606 반응식
[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][CH2:7][CH2:8][C:9]1([C:28]#N)[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:45]>COCCOC>[C:1]([Si:5]([CH3:30])([CH3:31])[O:6][CH2:7][CH2:8][C:9]1([CH:28]=[O:45])[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([F:26])([F:25])[F:27])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1)([CH3:3])([CH3:2])[CH3:4]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 21225700DiisobutylaluminumhydrideHCID 579664524-[2-(t-Butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

생성물 1

HCID 579663684-[2-(t-Butyldimethyl silanyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carboxaldehyde수율 87%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 4-[2-(t-butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile (600 mg) in 1,2-dimethoxyethane (12 mL) was added diisobutylaluminum hydride (1.0 M toluene solution, 6.39 mL) at 0° C. The mixture was stirred for 4 hours. To the reaction solution was added aqueous citric acid solution and extracted with ethyl acetate. The organic layer was sequentially washed with aqueous citric acid solution, water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (526 mg). Yield: 87%.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with aqueous citric acid solution, water and brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

출처 및 근거

ORD 기록
ord-2925e47cd1d7440da6bbcccc25ac52ea
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097610B2

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