Hydrogen Peroxide → 2-Oxaspiro[3.5]nonane-7-methanol

HRID 1043225Notes

Reaction equation

HRID 1043225 reaction equation
[O:1]1[CH2:5]CC[CH2:2]1.[CH:6]12B[CH:10]([CH2:11][CH2:12][CH2:13]1)[CH2:9][CH2:8]C2.[OH-:15].[Na+].OO>C(O)C>[CH2:2]1[C:12]2([CH2:11][CH2:10][CH:9]([CH2:8][OH:15])[CH2:6][CH2:13]2)[CH2:5][O:1]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane

Product 1

HCID 671267222-Oxaspiro[3.5]nonane-7-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 25 mL round-bottomed flask was added EXAMPLE 440E (568 mg) and tetrahydrofuran (4.11 mL). 9-Borabicyclo[3.3.1]nonane (0.5 M in tetrahydrofuran, 24.7 mL) was added and the reaction was allowed to stir for 2 hours at room temperature. Ethanol (11 mL) was added followed by NaOH (5M, 4.11 mL) and then hydrogen peroxide (2.1 mL) was added. The reaction was heated at 50° C. for 2 hours. Most of the ethanol and tetrahydrofuran was removed by rotary evaporation, and the crude material was diluted with water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (3×) and the combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by regular phase flash column chromatography (Analogix, 0-70% hexanes/ethyl acetate).

Workup

  1. temperatureThe reaction was heated at 50° C. for 2 hours
  2. customMost of the ethanol and tetrahydrofuran was removed by rotary evaporation
  3. additionthe crude material was diluted with water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  5. dry with materialthe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by regular phase flash column chromatography (Analogix, 0-70% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c214f632ec054dc29b5fc8e17ffc3531
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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