1.1: 100 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: NaH / dimethylformamide / 0.33 h / 20 °C 2.2: 52 percent / dimethylformamide / 14 h / 90 °C 3.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme

1: malonic acid dibenzyl ester; trans-4-fluorocinnamaldehyde With (S)-[α,α-bis(3,5-bistrifluoromethyl)phenyl]-2-pyrrolidine methanol trimethylsilyl ether in ethanol T=0°C; 96 h; 2: benzylamine With sodium tris(acetoxy)borohydride in 1,4-dioxane T=0 - 20°C; 24 h; 3: With lithium aluminium tetrahydride in tetrahydrofuran Heating; Title compound not separated from byproducts;

borane-THF in tetrahydrofuran

1.1: CuI / tetrahydrofuran 2.1: DIAD; PPh3 / tetrahydrofuran / -78 °C 3.1: tetrahydrofuran / 2 h 4.1: H2O2; KF; KHCO3 / 60 - 65 °C 5.1: Imidazole 6.1: O3 / propan-1-ol / -70 °C 6.2: Me2S / propan-1-ol 7.1: NaBH4 / propan-1-ol / 0 °C 8.1: I2; Imidazole; PPh3 9.1: dioxane / 2 h / 115 °C 10.1: 76 percent / Bu4NF View Scheme

1.1: CuI / tetrahydrofuran 2.1: DIAD; PPh3 / tetrahydrofuran / -78 °C 3.1: tetrahydrofuran / 2 h 4.1: H2O2; KF; KHCO3 / 60 - 65 °C 5.1: Imidazole 6.1: O3 / propan-1-ol / -70 °C 6.2: Me2S / propan-1-ol 7.1: NaBH4 / propan-1-ol / 0 °C 8.1: I2; Imidazole; PPh3 9.1: dioxane / 2 h / 115 °C 10.1: 76 percent / Bu4NF View Scheme

1.1: LiHMDS / tetrahydrofuran / 0.75 h / -78 °C 1.2: tetrahydrofuran / 1.2 h / -78 - -20 °C 2.1: H2O2 / CH2Cl2 / 0.5 h / 0 °C 3.1: 97 percent / tetrahydrofuran / 2 h / -78 °C 4.1: 44 percent / BH3*THF / tetrahydrofuran / 1.5 h / 0 °C 5.1: MsCl / 1,2-dichloro-ethane / 1 h / 0 - 20 °C 5.2: 84 percent / Et3N / 1,2-dichloro-ethane / 48 h / Heating 6.1: 71 percent / n-Bu3SnH / AIBN / toluene / 2 h / Heating 7.1: 100 percent / LAH / tetrahydrofuran / 0.83 h / 0 - 20 °C View Scheme

1.1: 97 percent / tetrahydrofuran / 2 h / -78 °C 2.1: 44 percent / BH3*THF / tetrahydrofuran / 1.5 h / 0 °C 3.1: MsCl / 1,2-dichloro-ethane / 1 h / 0 - 20 °C 3.2: 84 percent / Et3N / 1,2-dichloro-ethane / 48 h / Heating 4.1: 71 percent / n-Bu3SnH / AIBN / toluene / 2 h / Heating 5.1: 100 percent / LAH / tetrahydrofuran / 0.83 h / 0 - 20 °C View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 20 h; Heating;

1.1: [3H]-Caproic acid / ethanol / 70 - 150 °C / |Reflux 2.1: iodine / acetonitrile / 24 h / 0 °C / |Inert atmosphere; |Darkness 3.1: sodium carbonate / methanol / |Inert atmosphere; |Reflux 4.1: (S,S)-(salen)Co(OAc) complex; water / 12 h / 0 - 25 °C / |Resolution of racemate 5.1: triethylamine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 8 h / 80 °C 7.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 °C 8.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 9.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 10.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 10.2: 0.25 h / 20 °C / |Inert atmosphere 11.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 11.2: 48 h / 0 °C / |Inert atmosphere 12.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 13.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

1.1: iodine / acetonitrile / 24 h / 0 °C / |Inert atmosphere; |Darkness 2.1: sodium carbonate / methanol / |Inert atmosphere; |Reflux 3.1: (S,S)-(salen)Co(OAc) complex; water / 12 h / 0 - 25 °C / |Resolution of racemate 4.1: triethylamine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 5.1: sodium azide / N,N-dimethyl-formamide / 8 h / 80 °C 6.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 °C 7.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 8.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 9.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 9.2: 0.25 h / 20 °C / |Inert atmosphere 10.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 10.2: 48 h / 0 °C / |Inert atmosphere 11.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 12.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme