Sodium hydride → Tert-butyl 4-[2-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazol-2,4'-piperidin]-1'-yl)-2-oxoethyl]piperazine-1-carboxylate

HRID 856373Notes

Reaction equation

HRID 856373 reaction equation
Cl[C:2]1[N:3]([CH2:10][C:11]2([OH:33])[CH2:16][CH2:15][N:14]([C:17](=[O:32])[CH2:18][N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:13][CH2:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[H-].[Na+]>O1CCOCC1>[N+:7]([C:5]1[N:6]=[C:2]2[N:3]([CH:4]=1)[CH2:10][C:11]1([CH2:16][CH2:15][N:14]([C:17](=[O:32])[CH2:18][N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:13][CH2:12]1)[O:33]2)([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23081304Tert-butyl 4-{2-[4-(2-chloro-4-nitroimidazol-1-ylmethyl)-4-hydroxypiperidin-1-yl]-2-oxoethyl}piperazine-1-carboxylate

Product 1

HCID 69480722Tert-butyl 4-[2-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazol-2,4'-piperidin]-1'-yl)-2-oxoethyl]piperazine-1-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-{2-[4-(2-chloro-4-nitroimidazol-1-ylmethyl)-4-hydroxypiperidin-1-yl]-2-oxoethyl}-piperazine carboxylate prepared in Example 650 (2.58 g, 5.3 mmol) was dissolved in dioxane (30 ml). To the solution, sodium hydride (254 mg, 6.36 mmol) was added with cooling on ice-bath followed by stirring under reflux overnight. The reaction mixture was concentrated under reduced pressure. To the residue, ice-water and ethyl acetate were added followed by stirring vigorously. The precipitates were filtered off, washed with water and ethyl acetate, and then dried under reduced pressure to afford tert-butyl 4-[2-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazol-2,4′-piperidine]-1′-yl)-2-oxoethyl]piperazine-1-carboxylate (996 mg, yield 42%) as a white powder.

Workup

  1. temperaturewith cooling on ice-bath
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue, ice-water and ethyl acetate were added
  5. stirringby stirring vigorously
  6. filtrationThe precipitates were filtered off
  7. washwashed with water and ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-02ceae851076404382a5b933d38019b5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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