Dichloromethane → 1-((3-Bromofuran-2-yl)methyl)pyrrolidine

HRID 2190258

Reaction equation

HRID 2190258 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=O.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH2:7][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31268PyrrolidineHCID 33672713-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 710658951-((3-Bromofuran-2-yl)methyl)pyrrolidineYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromofuran-2-carbaldehyde (1.5 g, 8.57 mmol) and pyrrolidine (1.42 mL, 17.14 mmol) and CH2Cl2 (30 mL) was added sodium triacetoxyborohydride (3.63 g, 17.14 mmol). The mixture was stirred at room temperature for 5 hours. The resulting mixture was diluted with EtOAc (300 mL) and the organic layer was washed with saturated NaHCO3 and brine then dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2) to afford the sub-title compound (1.26 g, 65%).

Workup

  1. washthe organic layer was washed with saturated NaHCO3 and brine
  2. dry with materialthen dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica, 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9a38e33b6d0f452ea1095034341dbbae
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Linked notes

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