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N,N,N',N',N'',N''-hexamethylphosphoric triamide; lithium diisopropyl amide in tetrahydrofuran -78 deg C to RT;

1.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere View Scheme

sodium phosphate buffer; lipase from Candida rugosa 14 h; pH 7.2; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 0 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3.1: potassium hydroxide; water / methanol / 24 h / Reflux 3.2: pH 3 4.1: sodium hydroxide / water; acetone 5.1: bromine / hexane / 1 h / 20 °C 6.1: sodium hydroxide; water / 24 h / Reflux View Scheme

1: 56 percent / Na/K / diethyl ether / 0.5 h / Heating 2: 85 percent / Br2 / diethyl ether; hexane / 0.08 h / 0 °C 3: 75 percent / tert-butyllithium / tetrahydrofuran; dimethylsulfoxide / 5 h / 0 °C View Scheme

1,3-dimethyl-imidazolidin-2-one; ammonia; stannous oxide T=280°C; 48 h; Inert atmosphere; ConcentrationTime;

ammonia; stannous oxide T=210 - 280°C; 9 h; ConcentrationReagent/catalystTime; Overall yield = 90.2 percent;

1: 72 percent / LDA, HMPA / tetrahydrofuran / -78 deg C to RT 2: 50 percent / KOH / methanol; H2O / 24 h / 50 °C 3: 80 percent / BH3-THF / 24 h View Scheme