18366-41-1

Upstream product

• 96-09-3 styrene oxide 
• 5577-67-3 trimethyl(tert-butylamino)silane 
• 37167-62-7 bromo-phenyl-acetic acid methyl ester 
• 75-64-9 tert-butylamine 
• 100-52-7 benzaldehyde 
• 41804-43-7 methyl 2-(tert-butylamino)-2-phenylacetate 

Downstream Products

• 18366-82-0 3-tert-butyl-4r-phenyl-[1,2,3]oxathiazolidine 2c-oxide 
• 18366-82-0 3-tert-butyl-4r-phenyl-[1,2,3]oxathiazolidine 2t-oxide 

Relevant academic research and scientific papers

Continuous and convergent access to vicinyl amino alcohols

Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.

CONTINUOUS FLOW SYNTHESIS OF AMINO ALCOHOLS USING MICROREACTORS

The present invention provides various methods for the synthesis of chemical species in a microreactor environment. In some cases, reaction products of the present invention may be valuable as intermediates and/or products in pharmaceutical and polymer research. For example, the method may involve the synthesis of amino alcohols within a microchannel. Embodiment described herein may allow for reactions with significantly shorter reaction times and increased efficiency.

Metallocene catalyzed synthesis of fungistatic vicinal aminoalcohols under solvent free conditions

Group 4 and 5 metallocenes, Cp2TiCl2, Cp 2ZrCl2 and Cp2VCl2, have been evaluated as catalyst in the solvent free, room temperature, preparation of vicinal aminoalcohols. The regioselectivity of the reaction and the fungistatic activity of the prepared compounds against Botrytis cinerea and Colletotrichum gloeosporioides are discussed.

Aminolysis of epoxides in a microreactor system: A continuous flow approach to β-Amino alcohols

The use of a continuous flow microreactor for β-amino alcohol formation by epoxide aminolysis is evaluated. Comparison to microwave batch reactions reveals that conditions obtainable in the microreactor can match or improve yields in many cases. By increasing the pressure of the system, maximum temperatures can also exceed those accessible using a microwave unit. The use of a microreactor for epoxide aminolysis reactions in the synthesis of two pharmaceutical relevant compounds is described.

Hydrophobic amplification of noncovalent organocatalysis

The effects of hydrogen-bonding organocatalysts and water for the acceleration of epoxide openings with a variety of nucleophiles are additive and lead to excellent yields of the catalyzed reactions in water. The Royal Society of Chemistry 2006.

Highly chemoselective addition of amines to epoxides in water

(Chemical Equation Presented) Aminolysis of a variety of epoxides by aliphatic and aromatic amines in water, in the absence of any catalyst with high yields, is reported. β-Amino alcohols were formed under mild conditions with high selectivity and in excellent yields.

Solid lithium perchlorate as a powerful catalyst for the synthesis of β-aminoalcohols under solvent-free conditions

Lithium perchlorate catalyzed the ring opening of epoxides with amines to provide the corresponding β-aminoalcohols in excellent yields with high regioselectivity. The reaction proceeds rapidly under mild and neutral conditions and worked well with primary, secondary, aliphatic, aromatic, and hindered amines in short times at room temperature, in the absence of solvent.

Diisopropoxyaluminium trifluoroacetate: A new promoter for aminolysis of epoxides

Aminolysis of symmetrical as well as unsymmetrical epoxides using various amines in the presence of diisopropoxyaluminium trifluoroacetate (DIPAT) as a new promoter gave 1,2-amino alcohols in excellent yields at room temperature with good to excellent selectivities.

Lithium trifluoromethanesulfonate-catalysed aminolysis of oxiranes

The aminolysis of oxiranes was found to be catalysed by lithium trifluoromethanesulfonate in acetonitrile solutions. This salt turned out to be an excellent substitute for the unsafe lithium perchlorate.

Organoimido Complexes as a New Class of Lewis Acid Catalysts for Regioselective Ring-Opening of Epoxides

Organoimido complexes of Group VI transition metals were found to catalyze ring-opening of epoxides by trimethylsilyl azide and amines with good regioselectivities.