Hydrogen Peroxide → (-)-cis-Myrtanol

Borane-diisoamyl sulfide (5.0 ml, 21 mmol) was dissolved in THF (20 ml) and (-)-β-pinene (8.86 g, 64 mmol), [α]23D=-20.8° (neat), 91% ee, was added at 0° C. The mixture was kept at room temperature for 1 h and oxidized by the addition of 3M sodium hydroxide (10 ml, 30 mmol) and 30% hydrogen peroxide (7 ml, 70 mmol) keeping the temperature during the addition below 30° C. and then stirring at room temperature for 3 h. The mixture was saturated with potassium carbonate, the THF layer was separated and the aqueous layer was extracted with diethyl ether (2×50 ml). The extracts were combined with the THF solution, dried over magnesium sulfate and distilled using a Widmer column to give a first fraction, 4.25 g, bp 45°-58° C./0.1 mm Hg composed of diisoamyl sulfide (77%) and cis-myrtanol (23%) and a second fraction 7.96 g (82%), bp 58°-60° C./0.1 mm Hg, n20D=1.4907, [α]°D=-19.4° (neat).

1. additionduring the addition below 30° C.
2. customthe THF layer was separated
3. extractionthe aqueous layer was extracted with diethyl ether (2×50 ml)
4. dry with materialdried over magnesium sulfate
5. distillationdistilled
6. customto give a first fraction, 4.25 g, bp 45°-58° C./0.1 mm Hg
7. customn20D=1.4907, [α]°D=-19.4° (neat)

ORD record

ord-ed64b13e10ef4a3293adf617ddbf550e

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05567849