5-(4-Methoxyphenyl)-1-methyl-1,5-azaborocane-3,7-dione synthesis

Yield:1257739-11-9 70%

Reaction Conditions:

at 130; under 12929 Torr; for 0.0833333 h;Microwave irradiation;

Steps:

25 3.4. General procedure for MIDA boronate formation with PEG 300 (general method C)

General procedure: The boronic acid (1 mmol) was added to a 10 mL microwave vial equipped with a magnetic stirrer, and then PEG 300 (1 mL) was added followed by methyliminodiacetic acid (MIDA) (147 mg, 1 mmol). The Teflon cap was added and the reaction was heated using the dynamic heating method, with max power set to 40 W, max pressure 250 psi, max temperature 130 °C, high stirring throughout and power max turned off. This method was used to hold the reaction mixture at 130 °C for 5 min. After cooling, the mixture was added to water (9 mL). This mixture was stirred forming a white precipitate, then cooled in an ice bath allowing flocculation, then collected by filtration and washed with cold water (5 mL). The precipitate was allowed to dried in an oven set to 100 °C, giving pure product as a white precipitate (if not otherwise quoted). Notes: The 5 mmol scale reaction was performed using a 35 mL microwave vial and the 10 mmol scale was carried out usinga 100 mL round bottomed flask with a small air condenser attached with the open vessel attenuator installed. The heating parameters were kept the same but the hold time was changed to 7.5 min for the 5 mmol scale and 10 min for the 10 mmol scale reactions.

References:

Close, Adam J.;Kemmitt, Paul;Emmerson, Matthew K.;Spencer, John [Tetrahedron,2014,vol. 70,# 47,p. 9125 - 9131]