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Tetrabutylammonium Fluoride → Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate

HRID 1023327
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HRID 1023327 반응식
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O.O>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)=[CH:29][CH:30]=1
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참가 물질

6

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 67327082HCID 67327082, 화합물

생성물 1

HCID 67328866Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate수율 77.7%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회
HCID 8857
Ethyl Acetate
용매

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온도
0 °C

실험 절차

To a THF (8 mL) solution of tert-butyl 4-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)benzyl]piperazine-1-carboxylate (0.96 g) was added 1.0 M solution of TBAF in THF (2.32 mL) at 0° C. The resultant mixture was stirred at room temperature for 2.5 hours. After cooling to 0° C., the reaction mixture was diluted with AcOEt and water. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH=40/1) to afford tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (0.55 g) as a colorless oil.

후처리

  1. washThe organic layer was washed with saturated aqueous NaCl
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH=40/1)

출처 및 근거

ORD 기록
ord-220d01dedcfa460da7db884558a588ec
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722663B2

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