Multi-step reaction with 12 steps
1: 71 percent / sodium borohydride / tetrahydrofuran; ethanol / 0.5 h
2: 99 percent / triphenylphosphine; diethyl azidocarboxylate / tetrahydrofuran / 1 h / 20 °C
3: 95 percent / trifluoroacetic acid / CH2Cl2 / 16 h / 20 °C
4: 81 percent / K2CO3 / acetonitrile / 3 h / Heating
5: 10 percent / palladium(II) acetate; N,N'-bis(benzylidene)ethylenediamine; poly(methylhydrosiloxane) / acetic acid / benzene / 4 h / 95 °C
6: 97 percent / sodium borohydrate / methanol / 0.5 h
7: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C
8: 78 percent / sodium naphthalenide; sodium / 1,2-dimethoxy-ethane / 0.5 h / -50 °C
9: 97 percent / aq. NaBH3CN / acetonitrile / 0.25 h / 20 °C
10: 84 percent / platinum(II) oxide; H2 / methanol / 24 h / 3800 Torr
11: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C
12: 40 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 16 h / Heating
With
1H-imidazole; sodium tetrahydroborate; platinum(II) oxide; N,N'-bis(benzyliden)ethylendiamine; tetrabutyl ammonium fluoride; hydrogen; palladium diacetate; sodium; sodium naphthalenide; sodium cyanoborohydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; poly(methylhydrosiloxane); diethylazodicarboxylate;
acetic acid;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
2: Mitsunobu reaction / 12: Mitsunobu reaction;
DOI:10.1021/ja0401702