1: trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane With hydrogenchloride; zinc in methanol; water T=-5 - 0°C; 2: With ammonia in dichloromethane; water T=30°C; 0.25 h; 3: (R)-(-)-α-hydroxybenzeneacetic acid in methanol T=20 - 25°C;

in methanol T=20 - 25°C; 12 h;

1.1: AlCl3, aluminium chloride / dichloromethane / 4 h / 20 - 25 °C / Industry scale 2.1: sodium iodide; 1,3,5-trishydroxybenzene; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol; BH3*N,N-diethylanilline / toluene / 25 - 40 °C / Inert atmosphere 4.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 5.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 5.2: 0.25 h / 30 °C 5.3: 20 - 25 °C View Scheme

1.1: sodium iodide; 1,3,5-trishydroxybenzene; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol; BH3*N,N-diethylanilline / toluene / 25 - 40 °C / Inert atmosphere 3.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 4.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 4.2: 0.25 h / 30 °C 4.3: 20 - 25 °C View Scheme

1.1: (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol; BH3*N,N-diethylanilline / toluene / 25 - 40 °C / Inert atmosphere 2.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 3.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 3.2: 0.25 h / 30 °C 3.3: 20 - 25 °C View Scheme

1.1: sulfuric acid / 72 h / 60 °C 2.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 25 °C 2.2: 16 h / 0 - 25 °C 3.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 2.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 2.2: 0.25 h / 10 - 30 °C 3.1: methanol / 12 h / 20 - 25 °C View Scheme

1.1: pyridine / acetone / 0 h / 0 - 30 °C 1.2: 0 - 5 °C 2.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 2.2: 3 h / 25 - 30 °C 3.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme

1.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 1.2: 3 h / 25 - 30 °C 2.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 3.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 4.1: toluene / 1 h / 110 °C 4.2: 2 h / 100 °C 4.3: 25 °C / pH 10 5.1: methanol / 2.5 h / 18 - 45 °C View Scheme

1.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 1.2: 0.25 h / 10 - 30 °C 2.1: methanol / 12 h / 20 - 25 °C View Scheme