1: 1-methyl-pyrrolidin-2-one 2: HCl 3: (i) HOCH2CH2OH, TsOH, benzene, (ii) LiAlH4, Et2O, (iii) TsOH, acetone 4: Br2 / CHCl3 View Scheme

1: 1-methyl-pyrrolidin-2-one 2: HCl 3: Br2, HBr, AcOH / CHCl3 View Scheme

1-methyl-pyrrolidin-2-one

1: 80 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 130 deg C, 2 h then 200 deg C, 2 h 2: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux View Scheme

1: 71 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 6 h / 130 - 180 °C 2: magnesium turnings / tetrahydrofuran View Scheme

1: 80 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 130 deg C, 2 h then 200 deg C, 2 h 2: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux 3: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux View Scheme

1: 80 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 130 deg C, 2 h then 200 deg C, 2 h 2: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux 3: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux View Scheme

potassium fluoride; C94H134O4P2Pd2; silver fluoride in cyclohexane T=110°C; 14 h; Sealed tube;