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

HRID 2190260

반응식

HRID 2190260 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.C(Cl)Cl.[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.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)[O:5][CH:6]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27570104-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 86699373tert-Butyl 4-((4-bromofuran-2-yl)methyl)piperazine-1-carboxylate수율 91.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-bromofuran-2-carbaldehyde (500 mg, 2.85 mmol) and CH2Cl2 (10 mL) was added tert-butyl piperazine-1-carboxylate (1.06 g, 5.74 mmol) and sodium triacetoxyborohydride (1.2 g, 5.74 mmol). The mixture was stirred at room temperature overnight. The resultant mixture was diluted with EtOAc (100 mL), washed with brine then dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2) to afford the sub-title compound (900 mg, 91%).

후처리

  1. washwashed with brine
  2. dry with materialthen dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-9bea93ff56444fe3a645c33854574258
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324264B1

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