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

HRID 2190260

Reaction equation

HRID 2190260 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-9bea93ff56444fe3a645c33854574258
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Linked notes

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