Hydrogen Peroxide → HCID 68577163, compound

HRID 656470Notes

Reaction equation

HRID 656470 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]2=[CH2:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.[OH-:35].[Na+].OO>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH:13]2[CH2:25][OH:35])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 68576839HCID 68576839, compound

Product 1

HCID 68577163HCID 68577163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5 mmol of tert-butyl 2-benzyl-6-methylene-2,7-diazaspiro[4.5]decane-7-carboxylate in 60 ml of tetrahydrofuran is admixed at 0° C. with 10.6 mmol of 9-borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran). The reaction solution is stirred at 60° C. for 15 hours and then cooled to room temperature. The solution is admixed with 50 ml each of 3M sodium hydroxide solution and 30% hydrogen peroxide. The reaction mixture is stirred at room temperature for 2 hours. Subsequently the phases are separated and the aqueous phase is saturated with potassium carbonate and extracted with ethyl acetate (3×). The combined organic phases are dried over sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60 F) on the basis of the Rf value.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 2 hours
  3. customSubsequently the phases are separated
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined organic phases are dried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-51b2bd05b7014d67a0c29dc2fb2eb616
Source dataset
uspto-grants-2011_12
Patent number
US08071773B2

Reaction notes

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