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-f98b4d82b9b345829cc15626469c0a7c

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09243027B2