tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate in benzene 3 h; 0 deg C to RT;

1: 80 percent / HN3, DEAD, PPh3 / benzene / 3 h / 0 deg C to RT 2: H2 / Pd-C / methanol / 760 Torr / Ambient temperature 3: tetrahydrofuran / 6 h / Ambient temperature 4: imidazole / CH2Cl2 / 3 h / Ambient temperature 5: CF3COOH / CH2Cl2 / 3 h / 0 °C 6: DCC, HOBT / CH2Cl2 / 6 h / 0 deg C to RT 7: TBS-OTf, 2,6-lutidine / CH2Cl2 / 3 h / Ambient temperature 8: DCC, HOBT / CH2Cl2 / 5 h / -5 - 0 °C 9: HF-pyridine / CH2Cl2 / 4 h / Ambient temperature 10: LiOH / tetrahydrofuran; methanol; H2O / 3 h / Ambient temperature 11: DCC, DMAP, DMAP*TFA / CHCl3 / 16 h / Heating View Scheme