Acetone → methyl (2S)-2-(isopropylamino)butanoate

Temperature

0 °C

(2S)-2-Aminobutanoate 41b (13.14 g, 85.52 mmol) was dissolved in 200 mL of dichloromethane. The reaction solution was cooled down to 0° C. in an ice-water bath followed by the addition of sodium acetate (3.51 g, 42.76 mmol), acetone (5.96 g, 0.10 mol) and sodium triacetoxyborohydride (21.75 g, 0.10 mol) successively. The reaction solution was heated to room temperature and stirred for 4 hours. The resulting solution was added with 100 mL of water, added dropwise with saturated sodium carbonate solution to adjust pH to 11 to 12 and separated. The aqueous phase was extracted with dichloromethane (150 mL×2). The combined organic phase was washed with saturated brine (100 mL×2), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to obtain methyl (2S)-2-(isopropylamino)butanoate 43a (10.85 g, yield: 79.7%) as a light yellow oil.

1. temperatureThe reaction solution was heated to room temperature
2. customseparated
3. extractionThe aqueous phase was extracted with dichloromethane (150 mL×2)
4. washThe combined organic phase was washed with saturated brine (100 mL×2)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-d371c9a0182d40848fc4a91412742eb9

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2