sodium hypophosphite; hydrogen; nickel; palladium on activated charcoal 1) THF, 16 h, 2) pyridine - aq. acetic acid, RT, 4 h; Yield given. Multistep reaction;

hydrogen; palladium on activated charcoal in methanol P=3361.5 Torr; 0.75 h;

hydrogen; palladium on activated charcoal in tetrahydrofuran 12 h; var.solvents - benzene, methanol; var.ratio substrate/catalyst; var.pressure; Product distribution;

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: 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 4: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating View Scheme

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 4: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 5: tetrahydrofuran / 1 h / ice bath 6: NaBH4 / methanol View Scheme

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 4: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 5: tetrahydrofuran; H2O / 0.33 h / ice bath 6: NaBH4 / methanol; tetrahydrofuran; H2O / 0.25 h 7: 92 percent / K2CO3 / ethyl acetate; H2O / 0.08 h / ice bath 8: 87 percent / potassium t-butoxide / tetrahydrofuran / 0.33 h / Ambient temperature 9: 83 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

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 4: 77 percent / 2-pyrrolidinone hydrotribromide, pyrrolidinone / tetrahydrofuran / 3 h / Heating 5: tetrahydrofuran / 1 h / ice bath 6: NaBH4 / methanol View Scheme

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 View Scheme