1.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / water; butan-1-ol / 12 h / |Reflux 2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / methanol; water / 0.5 h / |Reflux 2.2: 12 h / 40 °C 3.1: L-CSA*1H2O / toluene / 49 h / 20 - 50 °C / |Resolution of racemate 3.2: 6 h / |Resolution of racemate; |Reflux View Scheme

N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide 12 h; Reflux;

1.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / water; butan-1-ol / 12 h / |Reflux; |Green chemistry 2.1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / methanol; water / 0.5 h / 10 - 40 °C / |Reflux; |Green chemistry 2.2: 12 h / 40 °C / |Green chemistry 3.1: (-)-10-CSA / water; toluene / 49 h / 20 - 50 °C / |Green chemistry 4.1: sulfuric acid / 12 h / 0 °C / |Green chemistry View Scheme

sodium hydrogencarbonate in methanol 3 h; Reflux;

1: sodium cyanide; 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride in methanol; water 0.666667 h; 2: 2-chloro-benzaldehyde in methanol; water T=23 - 50°C; 6 h; 3: With Na2S2O5 in methanol; water T=25 - 30°C; 2 h;

NaCN; sodium hydrogensulfite in water

sodium hydrogencarbonate in methanol 3 h; Heating / reflux; Product distribution / selectivity;

sodium hydrogencarbonate in butan-1-ol 3 h; Heating / reflux; Product distribution / selectivity;

in acetic acid; toluene

1: bromine / 6 h / 105 - 110 °C 2: sodium hydrogencarbonate / methanol / 3 h / |Reflux View Scheme