tetrakis(triphenylphosphine) palladium(0); cesium fluoride in 1,2-dichloro-ethane T=75°C; 6 h; Inert atmosphereSealed tube;

potassium tert-butylate in tetrahydrofuran 3 h; Heating;

1: 70 percent / H2 / 10percent Pd/C / methanol / 0.75 h / 3361.5 Torr 2: 2) dilute HCl / 1) THF-ether, reflux, 2 h, 2) steam bath, 5 min 3: 76 percent / potassium t-butoxide / tetrahydrofuran / 3 h / Heating View Scheme

1: 2) dilute HCl / 1) THF-ether, reflux, 2 h, 2) steam bath, 5 min 2: 76 percent / potassium t-butoxide / tetrahydrofuran / 3 h / Heating View Scheme

pyrrolidin-2-one; PHT in tetrahydrofuran 3 h; Heating;

1: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 2: tetrahydrofuran / 1 h / ice bath 3: NaBH4 / methanol View Scheme

1: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 2: tetrahydrofuran; H2O / 0.33 h / ice bath 3: NaBH4 / methanol; tetrahydrofuran; H2O / 0.25 h 4: 92 percent / K2CO3 / ethyl acetate; H2O / 0.08 h / ice bath 5: 87 percent / potassium t-butoxide / tetrahydrofuran / 0.33 h / Ambient temperature 6: 83 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 2: tetrahydrofuran / 1 h / ice bath 3: NaBH4 / methanol View Scheme