Hydrochloric Acid → 1-(2-Hydroxyethyl)piperazin-2-one
Reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C:12]1=[O:24])(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:24]Participants
4
Procedure
A mixture of tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylate (3.4 g, 9.50 mmol) and hydrogen chloride (15 ml of a 4M solution in 1,4-dioxane) in 1,4-dioxane (10 ml) was stirred at room temperature for 4 hour and then the mixture was evaporated. The residue was dissolved in a mixture of 5% methanol in dichloromethane (30 ml), basified with a 7N solution of ammonia in methanol and then filtered. The filtrate was evaporated and the residue was purified by silica gel chromatography eluting with 10% methanol in dichloromethane containing 0-5% 7M ammonia in methanol to give 1-(2-hydroxyethyl)piperazin-2-one (0.708 g, 57% yield) as a pale yellow oil.