1: 1-(mercaptomethyl)cyclopropane acetic acid dilithium salt; 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol methanesulfonate in tetrahydrofuran; hexanes T=-5°C; 8.5 h; 2: N,N-dicyclohexylamine in tetrahydrofuran; hexanes; ethyl acetate T=20°C; 1 h;

1: 2-[1-(mercaptomethyl)cyclopropyl]acetic acid methyl ester With sodium hexamethyldisilazane in tetrahydrofuran T=-15°C; 1 h; Inert atmosphere; 2: 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol methanesulfonate in tetrahydrofuran T=-15°C; 7 h; Inert atmosphere; Product distribution / selectivity;

1: 1-(mercaptomethyl)-cyclopropaneacetic acid With n-butyllithium in tetrahydrofuran; hexane T=-12.5°C; 1 h; Inert atmosphere; 2: 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol methanesulfonate in tetrahydrofuran; hexane T=-12.5 - -2.5°C; 6 h; Saturated solution; 3: With water; sodium chloride in tetrahydrofuran; hexane T=2.5 - 30°C; Product distribution / selectivity;

1: 1-(mercaptomethyl)-cyclopropaneacetic acid With sodium t-butanolate; PEG-600 in toluene T=-10°C; Inert atmosphere; 2: 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol methanesulfonate in tetrahydrofuran; toluene T=-10 - 20°C;

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -15 °C / Inert atmosphere 1.2: 7 h / -15 °C / Inert atmosphere 2.1: toluene / 20 - 80 °C 3.1: acetic acid / toluene; water / 0.33 h / 20 °C / pH 4 - 5 3.2: 0.5 h / 20 °C View Scheme