Hydrogen Peroxide → (1S,3S,5R)-6,8-Dioxabicyclo[3.2.1]octan-3-OL

The ditosylate derivative from Step 1 (107 g, 0.228 mmoL) was dissolved in THF (1.6 L) at -40° C. and Super-Hydride in THF (800 mL, 1M, 0.8 mmoL) was slowly added. The resulting reaction mixture was stirred at r.t. overnight. The reaction was cannulated into cold H2O (226 mL) using external cooling, then NaOH 3N (640 mL, 1.92 mmol) and H2O2 (30%) (490 mL, 4.3 mmol) were successively added. The reaction was stirred at r.t. for 1 hr. Then the supernatant (THF layer) was separated from the aqueous layer and concentrated. The resulting residue was combined with the aqueous layer and extracted with CH2Cl2 using a continuous extractor. The organic layer was dried (MgSO4) and evaporated to dryness. The oily residue was dissolved in hot Et2O, filtered and evaporated to dryness affording the title compound contaminated with the 2-octanol isomer. The crude product was used as such for the next step.

1. customThe resulting reaction mixture
2. stirringThe reaction was stirred at r.t. for 1 hr
3. customThen the supernatant (THF layer) was separated from the aqueous layer
4. concentrationconcentrated
5. extractionextracted with CH2Cl2 using a continuous extractor
6. dry with materialThe organic layer was dried (MgSO4)
7. customevaporated to dryness
8. dissolutionThe oily residue was dissolved in hot Et2O
9. filtrationfiltered
10. customevaporated to dryness

ORD record

ord-aee4af15198c42279d12afda2956c4ed

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05428060