1.1: N-methylmorpholine / acetonitrile / 1 h / -25 - -15 °C 2.1: acetonitrile; H2O / 1 h / -25 - -15 °C 3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -10 - -1 °C 3.2: hexane; tetrahydrofuran / 0.5 h 4.1: DIBAL 5.1: mercuric perchlorate trihydrate / propan-2-ol; CHCl3; H2O / 1 h / 20 °C 6.1: benzotriazole; 4 Angstroem molecular sieves / tetrahydrofuran / 17 h / 20 °C 6.2: 8.85 g / NaBH4 / tetrahydrofuran / 25 h / 20 °C View Scheme

1: Et3N / ethyl acetate / -30 °C 2: ethyl acetate; diethyl ether / 1.17 h 3: 23.0 g / HCl (g) / diethyl ether / -20 °C View Scheme

1: 4-methyl-morpholine / dichloromethane 2: diethyl ether 3: hydrogenchloride 4: sodium tetrahydroborate / ethanol View Scheme

sulfuric acid in methanol

acetic acid in tetrahydrofuran; dichloromethane; ethyl acetate

piperidine; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine in tetrahydrofuran T=20°C; ester cleavage; 2 h;

sodium tetrahydroborate in methanol T=20°C; 2 h;

1: With sodium hydrogencarbonate in water T=20 - 60°C; 2 h; 2: With hydrogenchloride in water

triphenylphosphine in tetrahydrofuran; NaHSO4; NaH; dichloromethane

copper in N,N-dimethyl-formamide T=120°C; 19 h;