Piperidine → HCID 57659744, compound

HRID 1897564Notes

Reaction equation

HRID 1897564 reaction equation
[C:1]([C:5]1[O:9][C:8]([CH2:10]Br)=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CC(C)=O.O>[C:1]([C:5]1[O:9][C:8]([CH2:10][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 12026771HCID 12026771, compound

Product 1

HCID 57659744HCID 57659744, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of methyl 5-tert-butyl-2-(bromomethyl)furan-3-carboxylate (0.28 g, 1.0 mmol) and piperidine (99 μL, 1 mmol) in acetone (5 mL) was stirred at room temperature 3 days. The mixture was diluted with water and extracted with EtOAc. The organic extracts were washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (0%-50% EtOAc-hexanes) to obtain methyl 5-tert-butyl-2-((piperidin-1-yl)methyl)furan-3-carboxylate (41 mg, 15% yield). LC/MS: m/z 280.3 (M+H)+ at 2.10 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel chromatography (0%-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b2f64f00c2a741f69c2b60a3f76d679b
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

Loading…