Tetrahydrofuran → (S)-2-methyl-3-phenylpropan-1-ol

Methyl (S)-2-methyl-3-phenylpropionate (5 mmol, 78.4% ee), sodium methoxide (1 mmol), a ruthenium complex 1 (0.01 mmol), and tetrahydrofuran (2 mL) were charged into a 100-mL autoclave equipped with a stirrer. Then, the mixture was subjected to hydrogenation at a hydrogen pressure of 5 MPa at 80° C. for 16 hours. The reaction solution was diluted with 20 mL of diethyl ether, and was passed through 8.9 g of silica gel. The silica gel was washed with diethyl ether. The obtained solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 13.4 g, hexane/ethyl acetate=8/1). (S)-2-Methyl-3-phenylpropanol (657 mg, 1% ee) was obtained.

1. customequipped with a stirrer
2. washThe silica gel was washed with diethyl ether
3. concentrationThe obtained solution was concentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (silica gel 13.4 g, hexane/ethyl acetate=8/1)

ORD record

ord-8feb2cb69ffa4a8e8a7c74b70bba3cca

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288575B2