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

HRID 2190256

Reaction equation

HRID 2190256 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-21fe05743de049d4a49b049ec970359d
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Linked notes

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