Tetrahydrofuran → Spiro[4.5]decane-8-methanol

Participants

Reaction Steps

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).

Provenance & Evidence