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tert-Butyl piperazine-1-carboxylate → (3-((4-(Tert-butoxycarbonyl)piperazin-1-yl)methyl)phenyl)boronic acid

HRID 564509
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HRID 564509 반응식
[CH:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)=O.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:24][C:21]([O:20][C:18]([N:12]1[CH2:17][CH2:16][N:15]([CH2:1][C:3]2[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=2)[CH2:14][CH2:13]1)=[O:19])([CH3:22])[CH3:23]
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참가 물질

6

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27343563-Formylphenylboronic acidHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 42609723(3-((4-(Tert-butoxycarbonyl)piperazin-1-yl)methyl)phenyl)boronic acid수율 120.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution of (3-formylphenyl)boronic acid (3.0 g, 20.0 mmol) in DCM (100 mL) was added 1,1-dimethylethyl 1-piperazinecarboxylate (3.91 g, 21.0 mmol), NaBH(OAc)3 (6.36 g, 30.0 mmol) and this mixture was stirred at room temperature for 17 h. The organic layer was diluted with EtOAc (100 mL), which was washed with H2O (30 mL), then dried over Na2SO4, filtered and concentrated to afford the title compound 7.72 g (quantitative). LC-MS m/z 321 (M+H)+, 1.49 min (ret time).

후처리

  1. washwas washed with H2O (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-16572614356e4330a72ef4a1fedd5993
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067408B2

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