Hydrogen Peroxide → HCID 67956886, compound

HRID 2208151Notes

Reaction equation

HRID 2208151 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[Si:15]([O:32][C@@H:33]1[CH2:38][CH2:37][C:36](=[O:39])[C@@H:35]([F:40])[CH2:34]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.OO.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1.C(OC)(C)(C)C>[Si:15]([O:32][C@@H:33]1[CH2:38][CH2:37][C@@H:36]([OH:39])[C@@H:35]([F:40])[CH2:34]1)([C:28]([CH3:31])([CH3:29])[CH3:30])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 3611392Lithium tri-s-butylborohydrideHCID 67957055HCID 67957055, compound

Product 1

HCID 67956886HCID 67956886, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

L-Selectride® (1M in THF; 69.0 mL; 69.0 mm0l) is dropped into a stirred solution of (2S*,4R*)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-fluorocyclohexanone (example C14; 23.3 g; 62.8 mmol) in dry THF (230 mL) at −15° C. The reaction mixture is stirred over night and cooled to 0° C. before careful addition of ice cold water (100 mL), followed by dropwise addition of H2O2 (30% solution in water; 39.0 mL). After 30 min. saturated Na2SO3-solution (80 mL) is dropwise added at 0° C. tert-BuOMe (300 mL) is added, the organic layer is separated and concentrated under reduced pressure. The aqueous layer is extracted with tert-BuOMe. All combined organic phases are washed with brine and dried over MgSO4. The solvent is removed under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/AcOEt—10:0 to 9:1) to yield 15.5 g of the title compound as colourless liquid.

Workup

  1. additionis added
  2. customthe organic layer is separated
  3. concentrationconcentrated under reduced pressure
  4. extractionThe aqueous layer is extracted with tert-BuOMe
  5. washare washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed under reduced pressure
  8. customThe residue is chromatographed on silica gel (cyclohexane/AcOEt—10:0 to 9:1)

Sources & evidence

ORD record
ord-8f95a836c2ef4c2caf84f3fd6082fa20
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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