Tetrahydrofuran → Spiro[4.5]decane-8-methanol

To a solution of spiro[4.5]dec-7-en-8-yl-methanol (0.7 g) obtained in Step 4 in a mixed solvent of tetrahydrofuran (7 mL)-methanol (7 mL) was added 5% palladium carbon (70 mg), followed by stirring the reaction mixture at room temperature under normal pressure in an atmosphere of hydrogen for 1.5 hours and then under increased pressure of 0.3 MPa in an atmosphere of hydrogen for 3 hours. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was dissolved in methanol (5 mL). To the solution was added sodium borohydride (0.14 g), followed by stirring the reaction mixture at room temperature for 30 minutes. After addition of 1N aqueous hydrochloric acid solution, the reaction mixture was extracted with ethyl acetate twice. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4) to give spiro[4.5]dec-8-yl-methanol (0.528 g).

1. filtrationThen, the reaction mixture was filtered through Celite
2. concentrationthe filtrate was concentrated
3. dissolutionThe residue was dissolved in methanol (5 mL)
4. additionTo the solution was added sodium borohydride (0.14 g)
5. additionAfter addition of 1N aqueous hydrochloric acid solution
6. extractionthe reaction mixture was extracted with ethyl acetate twice
7. washThe organic layer was washed with saturated brine
8. customdried
9. concentrationconcentrated
10. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:4)

ORD record

ord-31ccfced937b45f9904bb0e8d0550352

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299296B2