Water → HCID 57771508, compound

To a suspension of lithium aluminum hydride (55 mg) in tetrahydrofuran (5 mL) was added dropwise a solution of (4R)-4-benzyl-3-(spiro[5.5]undecane-2-carbonyl)-oxazolidin-2-one (chiral: A) (425 mg) obtained in Step 3 in tetrahydrofuran (5 mL) under ice-cooling and nitrogen atmosphere, followed by stirring the reaction mixture in the range of ice-cooling to room temperature for 1.5 hours. Then, to the reaction mixture were added successively water (0.06 mL), 4N aqueous sodium hydroxide solution (0.06 mL) and water (0.18 mL), followed by stirring the reaction mixture at room temperature for 30 minutes. The precipitated insolubles in the reaction mixture were filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:20 to 1:10) to give spiro[5.5]undec-2-yl-methanol (chiral: A)(185 mg).

1. temperaturecooling
2. stirringby stirring the reaction mixture at room temperature for 30 minutes
3. filtrationThe precipitated insolubles in the reaction mixture were filtered off
4. concentrationthe filtrate was concentrated in vacuo
5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:20 to 1:10)

ORD record

ord-73a35cf7814d4ea9b52785bf7d881680

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299296B2