Water → (3S)-3-hydroxy-3-phenylpropanenitrile

A mixed solvent (volume ratio=1:1, 5 mL) of water and methanol and the iridium aqua complex shown in the following Table 1 (0.5 mol % relative to 2-cyanoacetophenone) were mixed, and 2-cyanoacetophenone (1 mmol) and the hydrogen-donor compound shown in the following Table 1 (5 mmol) were added to the obtained solution at room temperature. The obtained mixture was stirred at 70° C. After confirming the disappearance of 2-cyanoacetophenone by thin layer chromatography, the reaction was quenched with brine (20 mL). The reaction mixture was subjected to extraction treatment (three times) with ethyl acetate (20 mL), and the obtained organic layers were combined. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=20:1) to give (S)-3-phenyl-3-hydroxypropionitrile. The conversion and optical purity are shown in Table 1.

1. additionwere mixed
2. additionwere added to the obtained solution at room temperature
3. customthe reaction was quenched with brine (20 mL)
4. extractionThe reaction mixture was subjected to extraction treatment (three times) with ethyl acetate (20 mL)
5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated
7. customThe obtained residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=20:1)

ORD record

ord-9cbc88f4a09b4a9f845edc4c55e681fc

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044224B2