Methyl 2,2-dimethylacetoacetate → (S)-3-Hydroxy-2,2-dimethyl-butyric acid methyl ester

Temperature

30 °C

The reaction is carried out in a 100-mL autoclave. 2,2-Dimethyl-3-oxo-butyric acid methyl ester (4.0 g, 27.8 mmol) is dissolved in 35 mL of degassed methanol under Argon atomosphere. Dichloro[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]ruthenium (II) (230.0 mg, 0.28 mmol) is added and the reaction mixture is purged with nitrogen twice and once with hydrogen. The autoclave is pressurized with hydrogen to 500 psi and stirred at 30° C. for 40 h. After this time, the reaction mixture is filtered through celite and concentrated under reduced pressure to provide 3.8 g of the title compound as a green oil with ee of 98%. Yield: 95%. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.15 (3H, d, J=6.4 Hz), 1.2 (6H, d, J=5.2 Hz), 2.6 (1H, br. S), 3.7 (3H, s), 3.9 (1H, q, J=6.4 Hz).

1. customthe reaction mixture is purged with nitrogen twice
2. filtrationAfter this time, the reaction mixture is filtered through celite and
3. concentrationconcentrated under reduced pressure

ORD record

ord-1f01dcea1f6f4adbb5228d26b0b92773

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372874B2