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%. 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%); nmax (CH2Cl2) 1685, 1543 and 1453 cm-1 ; dH (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. temperaturecooled to -70%
2. customthe cooling removed
3. stirringThe reaction mixture was stirred vigorously at ambient temperature for 15 minutes
4. additionCelite (2 g) added
5. filtrationThe mixture was filtered through Celite
6. washthe filter bed washed with dichloromethane and water
7. customevaporated to dryness under reduced pressure
8. customThe residue was evaporated from ethanol (2×)

ORD record

ord-4db3545922ba4e5fa83d4f6410a555f0

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05939066