1: With triphenylphosphine in tetrahydrofuran T=0 - 20°C; Staudinger reaction; Inert atmosphere; 2: With water in tetrahydrofuran Staudinger reaction;

1.1: chloramine-T / water; tert-butyl alcohol / 20 °C 1.2: 20 °C 2.1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 3.1: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 4.1: triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1.1: hydroxylamine hydrochloride; sodium hydroxide / water; tert-butyl alcohol / 4 h / 20 °C 2.1: chloramine-T / water; tert-butyl alcohol / 20 °C 2.2: 20 °C 3.1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 5.1: triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 2: triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1: triethylamine / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere 3: triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

1: N,N-dimethyl-formamide / 5 h / 20 °C 2: hydrazine hydrate / ethanol / 5 h / Reflux View Scheme

hydrazine hydrate in ethanol Gabriel reaction; 5 h; Reflux;

1: triethylamine / dichloromethane / 20 °C / Inert atmosphere 2: 5 Pd(II)/C(eggshell); hydrogen / ethyl acetate / 3 h / 20 °C View Scheme