Hydrogen Peroxide → HCID 90419029, compound

HRID 514870Notes

Reaction equation

HRID 514870 reaction equation
[CH2:1]([O:8][CH2:9][O:10][C:11]1([CH2:24][C:25]([CH3:27])=[CH2:26])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:28]O.[OH-].[Na+].O>C1COCC1>[CH2:1]([O:8][CH2:9][O:10][C:11]1([CH2:24][CH:25]([CH3:27])[CH2:26][OH:28])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 90418953HCID 90418953, compound

Product 1

HCID 90419029HCID 90419029, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 4-((benzyloxy)methoxy)-4-(2-methylallyl)piperidine-1-carboxylate (3.05 g, 8.1 mmol) in THF (50 mL) was added BH3 solution in THF (32 mL, 1 mol/L, 32.4 mmol), and the mixture was stirred at room temperature for 16 hrs. Then 30% H2O2 solution (30 mL) and 10% sodium hydroxide solution (50 mL) were added slowly to the mixture, and the mixture was stirred for another 2 hrs. The mixture was then treated with water (10 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by a standard method to give the product (1.97 g). LC-MS: m/z 394.5 (M+H)+

Workup

  1. stirringthe mixture was stirred for another 2 hrs
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by a standard method

Sources & evidence

ORD record
ord-5f8c0d1bbfad4363bb0b516189a79ce1
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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