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

HRID 2190256

反応式

HRID 2190256 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-21fe05743de049d4a49b049ec970359d
出典データセット
uspto-grants-2012_12
特許番号
US08324264B1

関連ノート

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