1: (S)-1,2,3,4-tetrahydro-5-hydroxy-N-propyl-naphthalen-2-ammonium hydrobromide With sodium carbonate in o-xylene; water T=70 - 80°C; 2: [2-(thien-2-yl)ethyl] 4-methylbenzenesulfonate With sodium carbonate in o-xylene Reflux;

sodium hydrogencarbonate in acetonitrile 9 h; Reflux;

1.1: acetonitrile; water / 2 h / 0 - 5 °C 2.1: potassium carbonate / toluene / 60 °C 3.1: hydrogen bromide / acetic acid / 3 h / Reflux 3.2: pH 12.5 3.3: pH 9 - 9.5 4.1: sodium hydrogencarbonate / acetonitrile / 9 h / Reflux 4.2: pH 1 - 2 4.3: pH 7 - 7.5 View Scheme

1.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 2.1: methyltretrahydrofuran, 2- / 75 °C 3.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 4.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 5.1: sodium carbonate / o-xylene; water / 70 - 80 °C 5.2: Reflux 5.3: 15 - 55 °C 6.1: ammonia / cyclohexane; water / Reflux View Scheme

1.1: sodium acetate; acetic acid; sodium tris(acetoxy)borohydride / tetrahydrofuran / 0 - 10 °C 1.2: 0.5 h / 0 - 20 °C 1.3: 1.33 h / 10 - 50 °C 2.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 5.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 6.1: sodium carbonate / o-xylene; water / 70 - 80 °C 6.2: Reflux 6.3: 15 - 55 °C 7.1: ammonia / cyclohexane; water / Reflux View Scheme

1.1: lauryl mercaptan / ethyl acetate / Inert atmosphere; Reflux 1.2: 0.58 h / Inert atmosphere; Reflux 1.3: 0.08 h / Reflux 2.1: potassium carbonate / 2-methyl tetrahydrofuran / Reflux 3.1: methyltretrahydrofuran, 2- / 75 °C 4.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 5.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 6.1: sodium carbonate / o-xylene; water / 70 - 80 °C 6.2: Reflux 6.3: 15 - 55 °C 7.1: ammonia / cyclohexane; water / Reflux View Scheme

1.1: hydrogen bromide / acetic acid / 3 h / Reflux 1.2: pH 12.5 1.3: pH 9 - 9.5 2.1: sodium hydrogencarbonate / acetonitrile / 9 h / Reflux 2.2: pH 1 - 2 2.3: pH 7 - 7.5 View Scheme

1.1: triethylamine / toluene / 4 h / 45 °C 2.1: sodium carbonate / o-xylene; water / 70 - 80 °C 2.2: Reflux 2.3: 15 - 55 °C 3.1: ammonia / cyclohexane; water / Reflux View Scheme

in 2-methylpropyl acetate T=110°C; 10 h; Product distribution / selectivity;

1.1: hydrogenchloride / water; tetrahydrofuran / 0.25 h / 65 °C 2.1: sodium hydrogensulfite; water; hydrogen bromide; acetic acid / 2 h / Reflux 3.1: sodium carbonate / o-xylene; water / 70 - 80 °C 3.2: Reflux 3.3: 15 - 55 °C 4.1: ammonia / cyclohexane; water / Reflux View Scheme