1.1: 88 percent / LiAlH4; diisopropylamine / tetrahydrofuran / 4 h / Heating 2.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C 3.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating 4.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C 5.1: AgOTf / CH2Cl2 / 1 h / 25 °C 5.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C 6.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C 7.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating 8.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C 9.1: 99 percent / HCl; methanol / 16 h / 25 °C 10.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C 10.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C 11.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C 12.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C 13.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C 14.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C View Scheme

sulfuric acid

ammonium hydroxide; hydrogen; nickel in methanol

2,4,6-trichloro-1,3,5-triazine; zinc(II) chloride in acetonitrile Beckmann rearrangement; 2 h; Heating;

1: LiAlH4, nBuNHMe / tetrahydrofuran View Scheme