Hydrogen Peroxide → (-)-cis-Myrtanol

HRID 1720126Notes

Reaction equation

HRID 1720126 reaction equation
B.[CH3:2][C:3]1([CH3:11])[C@H:9]2[CH2:10][C@@H:4]1[CH2:5][CH2:6][C:7]2=[CH2:8].[OH-:12].[Na+].OO>ClCCl>[CH3:2][C:3]1([CH3:11])[C@H:9]2[CH2:10][C@@H:4]1[CH2:5][CH2:6][C@H:7]2[CH2:8][OH:12]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 440967(-)-beta-Pinene

Product 1

HCID 11084102(-)-cis-MyrtanolYield 192.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 6.0M borane adduct (9i) was dissolved in dichloromethane (12 ml) and (-)-β-pinene (5.0 g, 26 mmol), 91% ee was added at 0° C. The reaction was completed in 0.5 h, as indicated in 11B NMR. The mixture was maintained at room temperature for 1 h and oxidized by the addition of 3M sodium hydroxide (5.6 ml, 17 mmol) and 30% hydrogen peroxide (4.0 ml, 40 mmol), keeping the temperature during the addition below 30° C. and then stirring at room temperature overnight. The dichloromethane layer was separated and stirred with water (20 ml) for 0.5 h. The organic layer was separated, dried over anhydrous magnesium sulfate and distilled to give 5.05 g (91%) of pure product, bp 116°-118° C./15 mm Hg. α!20D=-19.4°.

Workup

  1. additionduring the addition below 30° C.
  2. customThe dichloromethane layer was separated
  3. stirringstirred with water (20 ml) for 0.5 h
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-9d0759a08370432c99402895e599d800
Source dataset
uspto-grants-1996_04
Patent number
US05504240

Reaction notes

Loading…