Acetic Acid → (1s,3s,5r,6s)-5-{[Tert-butyl(dimethyl)silyl]oxy}-6-methyl-7-oxabicyclo[4.1.0]heptan-3-ol

The compound of Example 16C (9.20 g, 30.6 mmol) was dissolved in 105 mL of methanol. K2CO3 (10.1 g, 72.1 mmol, 2.35 equivalents) was added and the reaction mixture was stirred at ambient temperature for 2 hours. 6.60 mL (115 mmol, 3.77 equivalents) of acetic acid were added to the reaction mixture; after mixing for 10 minutes, the solids were filtered off and rinsed with 40 mL of methanol. The combined filtrate and rinses were concentrated to a residue which was mixed with 106 mL of water. The layers were separated, and the aqueous layer was extracted three times with 50 mL of ethyl acetate. The combined organic layers were washed twice with 45 mL of brine, dried over MgSO4, filtered and concentrated to afford the titled compound (7.72 g, 98%).

1. additionafter mixing for 10 minutes
2. filtrationthe solids were filtered off
3. washrinsed with 40 mL of methanol
4. concentrationThe combined filtrate and rinses were concentrated to a residue which
5. additionwas mixed with 106 mL of water
6. customThe layers were separated
7. extractionthe aqueous layer was extracted three times with 50 mL of ethyl acetate
8. washThe combined organic layers were washed twice with 45 mL of brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD-Eintrag

ord-2613d346a3a24dd887853b5dc7d0b75a

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08377913B2