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Dichloromethane → 1-((4-Bromofuran-2-yl)methyl)pyrrolidine

HRID 2190259
Notes
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Reaction equation

HRID 2190259 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.[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:3]=[C:4]([CH2:7][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[O:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31268PyrrolidineHCID 27570104-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 710659901-((4-Bromofuran-2-yl)methyl)pyrrolidineYield 61%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 4-bromofuran-2-carbaldehyde (500 mg, 2.85 mmol) and pyrrolidine (0.47 mL, 5.74 mmol) and CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (1.2 g, 5.71 mmol). The mixture was stirred at room temperature overnight. The resulting mixture was diluted with EtOAc (100 mL) and the organic layer was washed with brine then dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2) to afford the sub-title compound (400 mg, 61%).

Workup

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

Sources & evidence

ORD record
ord-b67cc13bde4c4d6d83486df538e77bc6
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324264B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes