Water → HCID 18183075, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine-2-carboxylate-8,8-dioxide (200 mg, 0.82 mmol) was dissolved in dry dichloromethane (minimum volume) under argon and cooled to -70° C. Diisobutylaluminium hydride (1.5M in toluene, 1 ml, 1.5 mmol) was added at <-70° C. and the mixture stirred at -70° C. until thin layer chromatography and infra-red spectroscopy showed little or no starting material remaining. Water (5 ml) was added carefully, cooling removed and the mixture stirred at ambient temperature for 1 h. Celite was added to the mixture and the resulting mixture filtered through a Celite pad. The Celite pad was washed with dichloromethane and water and the filtrate and washings combined and evaporated to dryness under reduced pressure. The residue was re-evaporated with ethanol (2×), triturated under diethyl ether and the product collected by filtration, washed with diethyl ether and dried in air (274 mg, 30%) (Found: M+ 200.0256. C7H8N2 O3S requires M 200.0253); nmax (Nujol) 1678, 1316, 1161 and 1191 cm-1 ; dH [250MHz; (CD3)2SO] 2.50-2.57 (2H, m), 3.81-3.85 (2H, m), 4.31 (2H, t, J 6Hz), 8.27 (1H, s), 9.80 (1H, s).

Provenance & Evidence