Water → HCID 19070278, compound

Temperature

-70 °C

Ethyl 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine-2-carboxylate (2.12 g, 10 mmol) was dissolved in dry dichloromethane (40 ml) under argon and cooled to -70° C. Diisobutylaluminium hydride (1.5M in toluene, 12 ml, 18 mmol) was added below -68° C. and the reaction mixture stirred at -70° C. for 1 h. Water was added carefully and the cooling removed. The reaction mixture was stirred vigorously at ambient temperature for 15 minutes and Celite (2 g) added. The mixture was filtered through Celite, the filter bed washed with dichloromethane and water, the filtrate and the washings combined and evaporated to dryness under reduced pressure. The residue was evaporated from ethanol (2×) to give the title compound as a white solid (1.31 g, 78%); νmax (CH2Cl2) 1685, 1543 and 1453 cm-1 ; δH (250 MHz; CDCl3) 2.34-2.43 (2H, m), 3.20 (2H, t, J 6 Hz), 4.17 (2H, t, J 6 Hz), 7.58 (1H, s), 9.75 (1H, s).

1. customthe cooling removed
2. stirringThe reaction mixture was stirred vigorously at ambient temperature for 15 minutes
3. additionCelite (2 g) added
4. filtrationThe mixture was filtered through Celite
5. washthe filter bed washed with dichloromethane and water
6. customevaporated to dryness under reduced pressure
7. customThe residue was evaporated from ethanol (2×)

ORD record

ord-58d86ca9b9894e53aa6a113703264919

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05602250