Methanol → Methyl 2-acetamidopropanoate

Participants

Reaction Steps

In a glove box, ((tert-Bu)2P(CH2)2P(Me)(tert-Bu))2Rh2Cl2 (4.1 mg, 0.005 mmol) was dissolved in 2 mL MeOH, followed by addition of AgBF4 (1.9 mg, 0.10 mmol, 2 equiv.). The solution turned from pale yellow to yellow with gray precipitates. After being stirred for 20 minutes the solution was filtered into a high-pressure tube containing a stir bar and one of the enamides (1 mmol, 100 equiv.). Another 3 to 5 mL MeOH was added and the solution generally turned lighter upon the addition of the enamide substrate. The vessel was then put under H2 of 30 to 40 Psig and stirred at room temperature. After the reaction was finished, the vessel was then take out of the glove box, and an aliquot of the reaction solution was taken from the vessel and analyzed directly or after work up to determine enantiomeric excess of the reaction product. Reaction of enamide (a) to form 2-acetylamino-propionic acid and reaction of enamide (b) to form 2-acetylamino-propionic acid methyl ester, yielded greater than 99% enantiomeric excess in both instances. Reaction of enamide (c) to form 2-acetylamino-3-phenyl-propionic acid and reaction of enamide (d) to form 2-acetylamino-3-phenyl-propionic acid methyl ester, yielded greater than 98% and 95% enantiomeric excess, respectively.

Provenance & Evidence