HCID 57771564, compound → HCID 57771601, compound

To a solution of spiro[4.5]dec-1-en-2-yl-methanol (50 mg) obtained in Step 5 of Example 15 in tetrahydrofuran (1 mL) was added 5% palladium carbon (5 mg), followed by stirring the reaction mixture under normal pressure in an atmosphere of hydrogen at room temperature for 20 hours. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was dissolved in methanol (1 mL). To the solution was added sodium borohydride (10 mg), followed by stirring the reaction mixture at room temperature for 1 hour. Then, after addition of 1N aqueous hydrochloric acid solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated to give spiro[4.5]dec-2-yl-methanol (30 mg).

1. filtrationThen, the reaction mixture was filtered through Celite
2. concentrationthe filtrate was concentrated
3. dissolutionThe residue was dissolved in methanol (1 mL)
4. additionTo the solution was added sodium borohydride (10 mg)
5. additionThen, after addition of 1N aqueous hydrochloric acid solution
6. extractionthe reaction mixture was extracted with ethyl acetate
7. washThe organic layer was washed with water
8. customdried
9. concentrationconcentrated

ORD record

ord-6808e96ef8924701b9586fac715501fd

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299296B2