2-amino-2-(3-chlorophenyl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.48 g, quantitative): 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.69 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.7 Hz, 3H), 7.21 (d, J=8.5 Hz, 2H), 6.83-6.72 (m, 3H), 6.67 (d, J=7.3 Hz, 4H), 6.39 (d, J=7.9 Hz, 1H), 5.09 (s, 1H), 3.14 (dd, J=10.7, 4.4 Hz, 1H), 2.93 (dd, J=10.7, 8.0 Hz, 1H); ESIMS m/z 518 ([M+H]+). isolated as a white solid (1.48 g, quantitative)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.48 g, quantitative): 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.69 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.7 Hz, 3H), 7.21 (d, J=8.5 Hz, 2H), 6.83-6.72 (m, 3H), 6.67 (d, J=7.3 Hz, 4H), 6.39 (d, J=7.9 Hz, 1H), 5.09 (s, 1H), 3.14 (dd, J=10.7, 4.4 Hz, 1H), 2.93 (dd, J=10.7, 8.0 Hz, 1H); ESIMS m/z 518 ([M+H]+). isolated as a white solid (1.48 g, quantitative)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol (Galley, G.; et al., WO 2008092785) and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an white solid (1.44 g, 99%): 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.66-7.53 (m, 3H), 7.25-7.08 (m, 2H), 6.77 (dd, J=8.6, 6.3 Hz, 4H), 6.70-6.61 (m, 4H), 6.58 (dd, J=6.4, 2.2 Hz, 1H), 6.49 (d, J=7.8 Hz, 1H), 5.18-4.95 (m, 1H), 3.43 (dd, J=11.3, 3.9 Hz, 1H), 3.31 (dd, J=11.3, 4.6 Hz, 1H); ESIMS m/z 534 ([M+H]+).

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of lithium borohydride in THF (10.5 ml, 2 M solution) under an argon atmosphere was added dropwise chlorotrimethylsilane (5.34 ml). The resulting suspension was cooled to 0° C. and amino-(3-chlorophenyl)-acetic acid (2.0 g) was added portionwise. The ice bath was removed and stirring at r.t. was then continued for 16 h. The mixture was quenched by dropwise addition of methanol (15 ml) and then concentrated in vacuo. The residue was suspended in ethyl acetate and washed with 2 N aq NaOH. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo to afford (RS)-2-amino-2-(3-chloro-phenyl)-ethanol (1.84 g, quant.) as a yellow viscous oil. MS (ISP): 174.2 ([{37Cl}M+H]+), 172.2 ([{35Cl}M+H]+). The ice bath was removed The mixture was quenched by dropwise addition of methanol (15 ml) concentrated in vacuo washed with 2 N aq NaOH The phases were separated the aqueous phase was extracted with ethyl acetate The combined organic phases were dried over sodium sulphate concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol and 3-(4-isothiocyanatophenyl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole and isolated as a white solid (1.48 g, quantitative): 1H NMR (300 MHz, CDCl3) δ 8.07 (s, 1H), 7.69 (d, J=8.4 Hz, 2H), 7.31 (d, J=8.7 Hz, 3H), 7.21 (d, J=8.5 Hz, 2H), 6.83-6.72 (m, 3H), 6.67 (d, J=7.3 Hz, 4H), 6.39 (d, J=7.9 Hz, 1H), 5.09 (s, 1H), 3.14 (dd, J=10.7, 4.4 Hz, 1H), 2.93 (dd, J=10.7, 8.0 Hz, 1H); ESIMS m/z 518 ([M+H]+). isolated as a white solid (1.48 g, quantitative)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with 2-amino-2-(3-chlorophenyl)ethanol (Galley, G.; et al., WO 2008092785) and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an white solid (1.44 g, 99%): 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.66-7.53 (m, 3H), 7.25-7.08 (m, 2H), 6.77 (dd, J=8.6, 6.3 Hz, 4H), 6.70-6.61 (m, 4H), 6.58 (dd, J=6.4, 2.2 Hz, 1H), 6.49 (d, J=7.8 Hz, 1H), 5.18-4.95 (m, 1H), 3.43 (dd, J=11.3, 3.9 Hz, 1H), 3.31 (dd, J=11.3, 4.6 Hz, 1H); ESIMS m/z 534 ([M+H]+).