Sodium triacetoxyborohydride → HCID 178434682, compound

To a solution of 3-methyl-1H-1,2,4-triazol-5-amine (1.6 g) in acetic acid (30 mL) was added (2R,6S)-2,6-dimethyltetrahydro-4H-pyran-4-one (2.5 g) at room temperature, and the mixture was stirred for 30 min. Sodium triacetoxyborohydride (5.2 g) was added, and the mixture was stirred at room temperature for 20 hr. Acetic acid was evaporated and ethyl acetate and water were added to the residue. The mixture was neutralized with sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in a small amount of ethyl acetate, and the mixture was crystallized from diisopropyl ether. The resulting solid was collected by filtration, washed with diisopropyl ether, and dried by heating under reduced pressure to give the title compound as a pale-yellow solid (0.75 g, 22%).

1. stirringthe mixture was stirred at room temperature for 20 hr
2. customAcetic acid was evaporated
3. additionethyl acetate and water were added to the residue
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in a small amount of ethyl acetate
9. customthe mixture was crystallized from diisopropyl ether
10. filtrationThe resulting solid was collected by filtration
11. washwashed with diisopropyl ether
12. customdried
13. temperatureby heating under reduced pressure

ORD record

ord-303dad2ca2bc449793cbcbd96e1e72b6

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148383B2