Water → 1-(2-Aminoethyl)-5,5-dimethylimidazolidine-2,4-dione

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Reaction Conditions

Reaction Steps

{2-[(Cyano-dimethyl-methyl)-amino]-ethyl}-carbamic acid tert-butyl ester (31.7 g, 139.5 mmol) was dissolved in dichloromethane (500 mL) and the stirred solution was cooled in an ice bath. After 15 min, chlorosulfonyl isocyanate (14.5 mL, 23.6 g, 167 mmol) was added by syringe over 2 min, and the resulting solution was stirred for an additional 30 min. The solution was concentrated in vacuo to give a pale yellow gum. Water (500 mL) was added, and the mixture was heated in an oil bath (bath temperature 101° C.) for 20 h, during which time the solid went into solution. The resulting pale brown solution was cooled and allowed to stand for 30 min before filtering through a fluted filter paper (removes a trace amount of an oily residue). The solution was applied to a 3″ diameter flash column packed with SCX ion exchange resin (800 g; Varian Cat# 12213040) which had been previously conditioned with MeOH (2 L) followed by water (2 L). The resin was washed with water (2 L) followed by MeOH (2 L), and the product was then eluted with 2 M NH3 in MeOH (2.4 L). Concentration in vacuo gave the product as a pale brown hygroscopic foam. This was dissolved in MeOH (150 mL), filtered through a fluted filter paper, and concentrated in vacuo to give pure product (16.7 g, 70%). Final purification was achieved by flash chromatography (DCM:MeOH:NH4OH; 80:20:1 v/v/v) to give a fluffy white solid. 1H NMR: δ (d6-DMSO, 400 MHz) 3.60 (bs, NH & H2O), 2.93 (2 H, t, CH2), 2.45 (2 H, t, CH2), 1.06 (6 H, S, C(Me)2). MS (M+H)+ 172.

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