Hydrogen Peroxide → HCID 9815732, compound

HRID 2296630Notes

Reaction equation

HRID 2296630 reaction equation
[CH2:1]([CH:4]1[N:10]2[C:11](=[O:14])[O:12][N:13]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].B.C(=O)(O)[O-:17].[Na+].OO>O1CCCC1.CO>[OH:17][CH2:3][CH2:2][CH2:1][CH:4]1[N:10]2[C:11](=[O:14])[O:12][N:13]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 516892Sodium BicarbonateHCID 9815533HCID 9815533, compound

Product 1

HCID 9815732HCID 9815732, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 6 (3.0 g, 0.0155 mol) in tetrahydrofuran (44 mL) under nitrogen was treated with a Borane.THF complex (1M, 18.56 mL) and this reaction was stirred for 2 hours. Methanol (2.50 mL) was added before a solution of saturated sodium bicarbonate (2.32 mL) and hydrogen peroxide (30%, 2.32 mL) were added resulting in a white precipitate. The precipitate was filtered off and the solvent was removed from the filtrate under reduced pressure to afford the title compound. 1H NMR (CDCl3, 300 MHz) d 1.2-2.5 (m, 8H), 2.59 (m, 2H), 2.95 (dd, 2H), 3.72 (m, 2H), 4.25 (m, 1H). 13C NMR (CDCl3, 75 MHz) d 23.87, 25.73, 26.23, 28.57, 31.88, 53.97, 61.90, 68.07, 159.9, 160.8.

Workup

  1. additionwere added
  2. customresulting in a white precipitate
  3. filtrationThe precipitate was filtered off
  4. customthe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-ec067f897f6544baa0cd6493c6c238b0
Source dataset
uspto-grants-2002_12
Patent number
US06489323B1

Reaction notes

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