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 6Hz), 4.17 (2H, t, J 6Hz), 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-c3a94af117f94b788bc47610fd774764

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05911985