tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-((3-bromofuran-2-yl)methyl)piperazine-1-carboxylate

HRID 2190256

반응식

HRID 2190256 반응식
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=O.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH2:7][N:12]1[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]1

참가 물질

6

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 33672713-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 71079128tert-Butyl 4-((3-bromofuran-2-yl)methyl)piperazine-1-carboxylate수율 92.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-bromofuran-2-carbaldehyde (500 mg, 2.85 mmol) and tert-butyl piperazine-1-carboxylate (1.1 g, 5.71 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (1.2 g, 5.71 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (100 mL). The organic phase was washed with aqueous NaHCO3 and brine then dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2) to afford the sub-title compound (910 mg, 92%).

후처리

  1. washThe organic phase was washed with aqueous NaHCO3 and brine
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-21fe05743de049d4a49b049ec970359d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324264B1

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