Hydrogen Peroxide → HCID 53939771, compound

HRID 1004956Notes

Reaction equation

HRID 1004956 reaction equation
[OH:1]O.[OH-].[Na+].[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH:15]3[O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]#[N:36])=[CH:13][C:8]=2[O:7][CH2:6]1>CO>[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH:15]3[O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35](=[O:1])[NH2:36])=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 14798Sodium Hydroxide2×HCID 53718569HCID 53718569, compound

Product 1

HCID 53939771HCID 53939771, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 ml of hydrogen peroxide (33%) and 0.2 ml of 2N sodium hydroxide solution were added to a solution of 236 mg (0.54 mmol) of tert-butyl (3RS,4RS)-4-benzo[1,3]dioxol-5-yl-3-(2-cyano-benzyloxy)-piperidine-1-carboxylate in 5 ml of methanol. The reaction solution was heated under reflux for 2 hours. Subsequently, the same amounts of hydrogen peroxide and sodium hydroxide solution were again added and the solution was heated for a further 2 hours. Thereafter, the solution was cooled and evaporated under reduced pressure. For purification, the residue was chromatographed on silica gel using a 9:1 mixture of methylene chloride and ether as the eluent. There were obtained 140 mg (57% of theory) of tert-butyl (3RS,4RS)-4-benzo[1,3]dioxol-5-yl-3-(2-carbamoyl-benzyloxy)-piperidine-1-carboxylate as a colourless solid; MS: 455 (M+H)+.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe solution was heated for a further 2 hours
  4. temperatureThereafter, the solution was cooled
  5. customevaporated under reduced pressure
  6. customFor purification
  7. customthe residue was chromatographed on silica gel using
  8. additiona 9:1 mixture of methylene chloride and ether as the eluent

Sources & evidence

ORD record
ord-7b964291ec8942b8b921a4dc1f445eec
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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