sodium carbonate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; water T=10 - 57°C; 6 h;

1: With sodium tetrahydroborate; calcium chloride in tetrahydrofuran; ethanol T=-7 - 5°C; 8.5 h; 2: With hydrogenchloride; water in tetrahydrofuran; ethanol; ethyl acetate T=5°C;

1: With sodium tetrahydroborate; calcium chloride in tetrahydrofuran; ethanol T=4 - 5°C; 0.583333 h; 2: tert-butyl (3S)-3-hydroxy-3-{6-[(methylamino)carbonyl]-2-naphthyl}-3-(1-trityl-1H-imidazol-4-yl)propanoate in tetrahydrofuran; ethanol; water T=23 - 29°C; 6 h; 3: With hydrogenchloride in tetrahydrofuran; ethanol; water

1.1: n-butyllithium; Di-n-butylmagnesium / hexane; tetrahydrofuran / 1.5 h / -11 - 20 °C / Inert atmosphere 1.2: 7.5 h / -11 °C 2.1: manganese(IV) oxide / isobutyramide / 60 h / 25 °C / Inert atmosphere 3.1: pyridine; cinchonine / tetrahydrofuran / 1.75 h / -25 °C / Inert atmosphere 4.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 8.5 h / -7 - 5 °C 4.2: 5 °C View Scheme

1.1: n-butyllithium; Di-n-butylmagnesium / hexane; tetrahydrofuran / 1.5 h / -11 - 20 °C / Inert atmosphere 1.2: 7.5 h / -11 °C 2.1: manganese(IV) oxide / isobutyramide / 60 h / 25 °C / Inert atmosphere 3.1: pyridine; cinchonine / tetrahydrofuran / 1.75 h / -25 °C / Inert atmosphere 4.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 8.5 h / -7 - 5 °C 4.2: 5 °C View Scheme

1.1: manganese(IV) oxide / isobutyramide / 60 h / 25 °C / Inert atmosphere 2.1: pyridine; cinchonine / tetrahydrofuran / 1.75 h / -25 °C / Inert atmosphere 3.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 8.5 h / -7 - 5 °C 3.2: 5 °C View Scheme

1.1: N,N-dimethyl-formamide; thionyl chloride / toluene / 1 h / 45 - 50 °C 1.2: 1 h / 10 - 25 °C 2.1: n-butyllithium; Di-n-butylmagnesium / hexane; tetrahydrofuran / 1.5 h / -11 - 20 °C / Inert atmosphere 2.2: 7.5 h / -11 °C 3.1: manganese(IV) oxide / isobutyramide / 60 h / 25 °C / Inert atmosphere 4.1: pyridine; cinchonine / tetrahydrofuran / 1.75 h / -25 °C / Inert atmosphere 5.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 8.5 h / -7 - 5 °C 5.2: 5 °C View Scheme