L-Selectridereg; in tetrahydrofuran T=-78°C; 2 h;

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 7 h;

[O3ReOSiPh3]; toluene-4-sulfonic acid in benzene T=80°C; 1 h;

4-bromooctafluorobutanetriethoxysilane; zinc diacetate in tetrahydrofuran T=40°C; 8 h; Inert atmosphere;

ammonium hydroxide in water 1) 0 deg C, 30 min, 2) r.t., 2 h;

1: in methanol T=20°C; 8 h; 2: With diisobutylaluminium hydride in hexane; toluene T=-78°C; 3: With sodium dihydrogenphosphate; sodium cyanoborohydride in methanol T=20°C; 8 h;

1: 94 percent / pyridine / 0.25 h / 0 °C 2: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 3: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 4: 83 percent / pyridine / 3 h / 0 °C 5: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 6: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 7: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 8: NaBH4 / methanol / 24 h / 20 °C 9: 46.3 mg / 48 h / Heating 10: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme

1: 83 percent / pyridine / 3 h / 0 °C 2: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 3: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 4: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 5: NaBH4 / methanol / 24 h / 20 °C 6: 46.3 mg / 48 h / Heating 7: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme

1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 2: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 4: NaBH4 / methanol / 24 h / 20 °C 5: 46.3 mg / 48 h / Heating 6: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme

1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 2: 83 percent / pyridine / 3 h / 0 °C 3: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 4: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 5: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 6: NaBH4 / methanol / 24 h / 20 °C 7: 46.3 mg / 48 h / Heating 8: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme