1: NaBH4 / ethanol / Ambient temperature 2: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.75 h / 120 °C 3: 2.) Et3N / 1.) RT, 20 h, 2.) ethyl acetate, RT, 1 h 4: 90 percent / N-benzylacridinium bromide / acetonitrile / Ambient temperature 5: H2 / Pd / 760 Torr 6: NaOEt / ethanol / 0.5 h / Heating View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.75 h / 120 °C 2: 2.) Et3N / 1.) RT, 20 h, 2.) ethyl acetate, RT, 1 h 3: 90 percent / N-benzylacridinium bromide / acetonitrile / Ambient temperature 4: H2 / Pd / 760 Torr 5: NaOEt / ethanol / 0.5 h / Heating View Scheme

1: POCl3, pyridine 2: NaBH4 / ethanol / Ambient temperature 3: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.75 h / 120 °C 4: 2.) Et3N / 1.) RT, 20 h, 2.) ethyl acetate, RT, 1 h 5: 90 percent / N-benzylacridinium bromide / acetonitrile / Ambient temperature 6: H2 / Pd / 760 Torr 7: NaOEt / ethanol / 0.5 h / Heating View Scheme

1: 2.) Et3N / 1.) RT, 20 h, 2.) ethyl acetate, RT, 1 h 2: 90 percent / N-benzylacridinium bromide / acetonitrile / Ambient temperature 3: H2 / Pd / 760 Torr 4: NaOEt / ethanol / 0.5 h / Heating View Scheme

1: 90 percent / N-benzylacridinium bromide / acetonitrile / Ambient temperature 2: H2 / Pd / 760 Torr 3: NaOEt / ethanol / 0.5 h / Heating View Scheme

1: 63 percent / n-BuLi / tetrahydrofuran / 1 h 2: POCl3 / pyridine / 1.) room temp, 1 h, 2:) 75 deg C, 1.5 h 3: NaBH4 / ethanol / 2 h 4: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 5: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 6: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 7: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 8: 50 percent / NaOEt / ethanol / 0.5 h / Heating View Scheme

1: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 2: 50 percent / NaOEt / ethanol / 0.5 h / Heating View Scheme

1: H2 / Pd / 760 Torr 2: NaOEt / ethanol / 0.5 h / Heating View Scheme