Sodium Bicarbonate → HCID 23081398, compound

HRID 856371Notes

Reaction equation

HRID 856371 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[O:10]1[C:12]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:11]1.C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:11][C:12]2([OH:10])[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateHCID 178526855HCID 178526855, compound

Product 1

HCID 23081398HCID 23081398, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-4-nitro-1H-imidazole (3.1 g, 21.0 mmol), tert-butyl 1-oxa-6-azaspiro[2,5]octane-6-carboxylate (4.4 g, 21.0 mmol) and sodium hydrogen-carbonate (1.94 g, 23.1 mmol) in ethanol (20 ml) were stirred under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added water. The resulting solution was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 4-(2-chloro-4-nitroimidazol-1-ylmethyl)-4-hydroxypiperidine-1-carboxylate (5.4 g, yield 72%) as a yellow oil.

Workup

  1. temperatureunder reflux for 6 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was added water
  4. extractionThe resulting solution was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-d2de68610aca4e8691e80061737043e8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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