Multi-step reaction with 11 steps
1.1: N,N-dimethyl-formamide / 20 °C / Heating
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 10 - 20 °C
3.1: N,N-dimethyl-formamide / 7 h / 140 °C / Inert atmosphere
4.1: sodium periodate / water; tetrahydrofuran / 1 h / 20 °C
5.1: piperidine; acetic acid / dichloromethane / 18 h / Reflux
6.1: pyridine; rac-Pro-OH / N,N-dimethyl-formamide / 192 h / Inert atmosphere; Molecular sieve
7.1: toluene-4-sulfonic acid; pyridine / toluene / 1 h / Reflux
8.1: triethylamine; pyridine / toluene / 2 h / Inert atmosphere; Reflux
9.1: triethylamine; pyridine; copper diacetate / dichloromethane / 12 h / Inert atmosphere; Molecular sieve
9.2: 84 h / Inert atmosphere
9.3: 120 h
10.1: hydrazine hydrate / ethanol / 1 h / 85 °C
11.1: pyridine / tetrahydrofuran / 12 h / 20 - 80 °C / Inert atmosphere
With
piperidine; pyridine; sodium periodate; copper diacetate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; rac-Pro-OH;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;