Multi-step reaction with 13 steps
1: hydrogenchloride / 6.17 h / 0 - 20 °C
2: triethylamine / dichloromethane / 0 - 20 °C
3: 1H-imidazole / dichloromethane / 20 °C
4: lithium triethylborohydride / tetrahydrofuran / 3.67 h / -78 - 20 °C
5: Dess-Martin periodane / 2 - 4 h / 0 - 20 °C
6: sodium tris(acetoxy)borohydride / acetic acid; 1,2-dichloro-ethane / 1 h / 20 °C
7: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
8: N-ethyl-N,N-diisopropylamine / dichloromethane; toluene / 2 h / 0 - 20 °C
9: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C
10: triethylamine / dichloromethane / 0.75 - 1 h / 0 °C
11: sodium azide / dimethyl sulfoxide / 24 h / 80 °C
12: triphenylphosphine / tetrahydrofuran; water / 48 h / 50 - 70 °C
13: 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
With
4-methyl-morpholine; 1H-imidazole; hydrogenchloride; sodium azide; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; water; acetic acid; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;