hydrogen; palladium on activated charcoal in tetrahydrofuran; water P=760 Torr; 3 h; Ambient temperature; Yield given;

1: TFA / CH2Cl2 / 0.5 h 2: H2 / 10percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr View Scheme

1: 92 percent / acetonitrile / 24 h / Ambient temperature 2: 78 percent / PPh3, CBr4 / tetrahydrofuran / Ambient temperature; 1.) 2 h, 2.) stirring overnight 3: 62 percent / KI, K2CO3 / acetone / 24 h / Heating 4: 92 percent / CF3COOH / 0.25 h / Ambient temperature 5: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 6: tetrahydrofuran; H2O / 2 h 7: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 57 percent / Et3N / CHCl3 / 72 h / Heating 2: 41 percent / DCC / acetonitrile / 1.) 0 deg C, 0.5 h, 2.) room temperature, 5 h 3: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 4: tetrahydrofuran; H2O / 2 h 5: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 78 percent / PPh3, CBr4 / tetrahydrofuran / Ambient temperature; 1.) 2 h, 2.) stirring overnight 2: 62 percent / KI, K2CO3 / acetone / 24 h / Heating 3: 92 percent / CF3COOH / 0.25 h / Ambient temperature 4: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 5: tetrahydrofuran; H2O / 2 h 6: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 62 percent / KI, K2CO3 / acetone / 24 h / Heating 2: 92 percent / CF3COOH / 0.25 h / Ambient temperature 3: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 4: tetrahydrofuran; H2O / 2 h 5: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 2: tetrahydrofuran; H2O / 2 h 3: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 41 percent / DCC / acetonitrile / 1.) 0 deg C, 0.5 h, 2.) room temperature, 5 h 2: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 3: tetrahydrofuran; H2O / 2 h 4: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 92 percent / CF3COOH / 0.25 h / Ambient temperature 2: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 3: tetrahydrofuran; H2O / 2 h 4: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme

1: 95.6 percent / Et3N / acetonitrile / 2.5 h / Ambient temperature 2: tetrahydrofuran; H2O / 2 h 3: H2 / 5percent Pd/C / tetrahydrofuran; H2O / 3 h / 760 Torr / Ambient temperature View Scheme