Water → Methyl 3alpha,7alpha-ditetrahydropyranyloxy-5beta-cholan-24-oate

p-Toluenesulfonic acid (78 mg, 0.41 mmol), 3,4-dihydro-2H-pyrane (20.1 ml, 0.098 mol) were added to a solution of methyl 3α,7α-dihydroxy-5β-cholan-24-oate (1) (2.0 g, 4.9 mmol) in dioxane (6 mL). The reaction mixture was stirred at room temperature for 15 min. H2O (50 mL) was then added and the mixture was partially concentrated under vacuum and extracted with EtOAc (3×50 mL). The combined organic fractions were washed with brine (1×50 mL), dried (Na2SO4) and evaporated under vacuum. The residue was purified by chromatography on silica gel column. Elution with light petroleum/ethyl acetate 80/20 afforded 2.5 g of the pure compound 2 (90% yield).

1. concentrationthe mixture was partially concentrated under vacuum
2. extractionextracted with EtOAc (3×50 mL)
3. washThe combined organic fractions were washed with brine (1×50 mL)
4. dry with materialdried (Na2SO4)
5. customevaporated under vacuum
6. customThe residue was purified by chromatography on silica gel column
7. washElution with light petroleum/ethyl acetate 80/20

ORD record

ord-9ed9279863094666a21c0826462977b8

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114862B2