Vinyl propanoate

Racemic l-dimethylaminopropan-2-ol (18) was acylated with propanoyl chloride, and the reaction product was analyzed by gas chromatography (GC). The resultant (R)- and (5)-esters 19 (R1 = COEt) were resolved by GC using an a-cyclodextrin column. Reaction of the racemic alcohol 18 was then carried out in the presence of Novozyme 435 and vinyl propanoate, and the reaction was followed by GC. After 4 hours the reaction was approximately 2% complete and the ee of the propanoate ester 19 (R1 = COEt) was 95.9%. After 88 hours the conversion had reached 50% and the ee was still 95.6%. The remarkable specificity of Novozyme 435 for the (/O-amino alcohol 1 A )-18 was evident because even after 3.5 days reaction time, only a very small amount of the (5)-ester was detected. The reaction could be scaled up thus, 1 kg of the racemic amino alcohol 18 was treated with vinyl propanoate (0.5 equivalents) and Novozyme 435 (3% by weight). After 3 days, both optically active products were isolated by distillation at reduced pressure. The (5)-amino alcohol (.V)-18 was recovered in 45% yield, which compared favorably with a yield of 32% for resolution on a small scale. The (R)-propanoate 19 (R1 = COEt) distilled as a colorless oil in 36% yield — slightly higher than that obtained from the small-scale resolution. The overall recovery was 81% from the scaled up reaction. 

Vinyloxirane 2-(Vinyloxy)ethanol Vinyl propanoate 2-Vinylpyridine 3-Vinylpyridine 4-Vinylpyridine 1-Vinyl-2-pyrrolidinone Vinylsilane Vinyl sulfoxide... 

C5H8O2 105-38-4 Propanoic acid vinyl ester see Vinyl propanoate... 

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