Abstract
An unprecedented two-step sequence was designed by combining batch and continuous flow (CF) protocols for the upgrading of two aminodiol regioisomers derived from glycerol, i.e., 3-amino-1,2-propanediol and 2-amino-1,3-propanediol (serinol). Under batch conditions, at 80–90 °C, both substrates were quantitatively converted into the corresponding amides through a catalyst-free N-acetylation reaction mediated by an innocuous enol ester as isopropenyl acetate (iPAc). Thereafter, at 30–100 °C and 1–10 atm, the amide derivatives underwent a selective CF-acetalisation in the presence of acetone and a solid acid catalyst, to afford the double-functionalized (amide-acetal) products.
Highlights
Thereafter, at 30–100 ◦ C and 1–10 atm, the amide derivatives underwent a selective continuous flow (CF)-acetalisation in the presence of acetone and a solid acid catalyst, to afford the double-functionalized products
N-acetylation were used without any treatment, to feed a CF-reactor for the second batch N-acetylation were used without any treatment, to feed a CF-reactor for the second acetalization acetalization step
Reagents and solvents were commercially available compounds and were used as received unless otherwise stated. 3-amino-1,2-propanediol, 2-amino-1,3-propanediol, isopropenyl acetate, 1,4-dioxane, dimethyl sulfoxide, ethanol, acetone, Amberlyst-15, AlF3 ·3H2 O were sourced from Sigma Aldrich ( Merck Life Science S.r.l., Milano, IT)
Summary
3-Amino-1,2-propanediol (3-APD) and 2-amino-1,3-propanediol (2-APD, serinol) are formally classified as glycerol derivatives obtained by the replacement of a primary or a. N.A.; Perosa, A.; Selva, M. secondary hydroxyl group of glycerol with a primary amine function. Concatenated Batch and Continuous categorization, no examples have been reported so far for the straightforward preparation
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