Potassium Carbonate → HCID 69419323, compound

HRID 1295575Notes

Reaction equation

HRID 1295575 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=2)=[O:25])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22326643HCID 22326643, compound

Product 1

HCID 69419323HCID 69419323, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(tert-butoxycarbonyl)-4-(4-hydroxy-3-nitrobenzoyl)piperidine (1.50 g, 4.3 mmol), potassium carbonate (0.77 g, 5.6 mmol), and methyl bromoacetate (0.66 g, 4.3 mmol) in acetone (20 mL) was stirred at reflux for 18 h. The reaction mixture was cooled and evaporated in vacuo, and the residue partitioned between water (20 mL) and dichloromethane (20 mL). The organic layer was separated and washed with 1N NaOH (aq) (20 mL), water (20 mL), and brine (10 mL), dried (Na2SO4) and evaporated in vacuo to give crude product which was purified by chromatography on silica gel (˜20 g) eluting with 10–100% EtOAc in hexane to give the title compound (0.85 g, 47%) as a yellow oil. 1H NMR (CDCl3) δ: 1.47 (9H, s), 1.62–1.89 (4H, m), 2.91 (2H, m), 3.35 (1H, m), 3.82 (3H, s), 4.17 (2H, m), 4.88 (2H, s), 7.04 (1H, d, J=9 Hz), 8.13 (1H, dd, J=9, 2 Hz), 8.44 (1H, d, J=2 Hz).

Workup

  1. temperatureat reflux for 18 h
  2. temperatureThe reaction mixture was cooled
  3. customevaporated in vacuo
  4. customthe residue partitioned between water (20 mL) and dichloromethane (20 mL)
  5. customThe organic layer was separated
  6. washwashed with 1N NaOH (aq) (20 mL), water (20 mL), and brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customto give crude product which
  10. customwas purified by chromatography on silica gel (˜20 g)
  11. washeluting with 10–100% EtOAc in hexane

Sources & evidence

ORD record
ord-e4eedb591e034c5aaa531a9de73e692a
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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