hydrogen; palladium on activated charcoal in methanol Yield given;

sodium hydroxide in tetrahydrofuran; water

1: NaNO2, HCl 2: KI 3: 94 percent / K2CO3 / acetone 4: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 5: 98 percent / Zn, AcOH 6: 96 percent / pyridine / CH2Cl2 7: 92 percent / triphosgene, Et3N / CH2Cl2 8: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 9: NaOH / H2O; tetrahydrofuran View Scheme

1: 94 percent / K2CO3 / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH2Cl2 5: 92 percent / triphosgene, Et3N / CH2Cl2 6: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H2O; tetrahydrofuran View Scheme

1: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 2: 98 percent / Zn, AcOH 3: 96 percent / pyridine / CH2Cl2 4: 92 percent / triphosgene, Et3N / CH2Cl2 5: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 6: NaOH / H2O; tetrahydrofuran View Scheme

1: H2 / Pd-C / methanol 2: DIBAL / CH2Cl2 / -78 °C 3: pyridine / CH2Cl2 / 0 °C 4: NaN3 / dimethylformamide 5: H2 / 10percent Pd-C / methanol View Scheme