Multi-step reaction with 13 steps
1: Zn(BH4)2, NH4Cl / diethyl ether / 0.33 h / 0 °C
2: PPh3, diisopropyl azodicarboxylate (DIAD) / tetrahydrofuran / 0.5 h
3: 100 percent / 55percent aq. NH2NH2*H2O / methanol / 0.25 h / 25 °C
4: PPTS / benzene / 3 h / 25 °C
5: 99 percent / 2,6-lutidine / CH2Cl2 / 0.42 h / -25 - 0 °C
6: 90 percent / DIBAL / CH2Cl2 / 0.75 h / -78 °C
7: acetonitrile / 16 h / 25 °C
8: DIBAL / CH2Cl2 / 2 h / -78 °C
9: Et3N, DMAP / CH2Cl2 / 12 h / 25 °C
10: TBAF, aq. AcOH / tetrahydrofuran / 0.25 h / 0 °C
11: K-Selectride / 1,2-dimethoxy-ethane; tetrahydrofuran / 1 h / -70 - -30 °C
12: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C
13: 81 percent / BH3*NH3, PPTS / tetrahydrofuran / 25 °C
With
2,6-dimethylpyridine; dmap; borane-ammonia complex; zinc(II) tetrahydroborate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium tri-sec-butyl-borohydride; ammonium chloride; hydrazine hydrate; acetic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; acetonitrile; benzene;