129348-90-9

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 108-24-7 acetic anhydride 
• 156-87-6 propan-1-ol-3-amine 
• 13609-09-1 N-(3-hydroxypropyl)benzamide 
• 98-88-4 benzoyl chloride 
• 107-10-8 propylamine 
• 64-19-7 acetic acid 
• 433925-63-4 3-[(tert-butoxycarbonyl)amino]propyl acetate 

Downstream Products

• 6638-35-3 2-phenyl-5,6-dihydro-4H-1,3-thiazine 
• 36926-17-7 N-(3-hydroxypropyl)benzothioamide 

Relevant academic research and scientific papers

Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines

An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S N 2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation-thionation-saponification sequence from commercially available ω-amino alcohols. The whole process is metal-free and operationally simple.

Transient Directing Group Enabled Pd-Catalyzed γ-C(sp3)-H Oxygenation of Alkyl Amines

We report a general protocol for γ-C(sp3)-H acyloxylation and alkoxylation of free amines using 2-hydroxynicotinaldehyde as the transient directing group. In the presence of an electrophilic fluorinating bystanding oxidant and acetic acid, a wide range of aliphatic amines could be oxygenated selectively at the γ-methyl positions. A vast variety of aryl, heteroaryl, and aliphatic acids could also be successfully coupled under this C-O bond formation reaction to afford amine-containing esters. Switching the nucleophile from acids to alcohols enables alkoxylation of free amines. Importantly, natural products and drug molecules such as ibuprofen, isoxepac, fenbufen, and lithocholic acid are all compatible coupling partners. Notably, synthesis of these monoprotected amino alcohols from free amino alcohols using conventional selective protection are not always feasible.

One-pot conversion of t-butyl carbamates to amides with acyl halide-methanol mixtures

Acyl halide-methanol mixtures are efficient reagents for the one-pot transformation of t-butyl carbamates into amides. This transformation can be carried out in the presence of a benzyloxycarbonyl group.

A novel electrochemical method for benzoylation of aminoalcohols with methyl benzoates at room temperature

A novel electrochemical method of benzoylating aminoalcohols 2 by use of methyl benzoates 1 at room temperature was developed. 2-Aminoethanols 2 (n=0, R3=H) and 3-aminopropanols 2 (n=1, R3=H) gave the corresponding benzamides 4, as a result of electrochemical transesterification followed by O,N-acyl migration.In contrast, o- and m-aminobenzylalcohols (7a and 7b) and trans-4-(aminomethyl)cyclohexanemethanol (8a) afforded the corresponding benzoic esters, since their acyl migration is hindered.A local anesthetic, procaine, was prepared by using this electrochemical reaction.A mechanism for electrochemical transesterification, which involves a formation of alcoholate anion by a one-electron reduction of alcohol, is presented.