Multi-step reaction with 10 steps
1: 1.3 kg / bromine, sodium acetate / acetic acid / 45 h
2: 76 percent / copper / pyridine / 16 h / 95 °C
3: 1.04 kg / K2CO3 / dimethylformamide / 75 °C
4: 1.45 kg / 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (ETB), triethylamine / 2 h / 90 °C
5: 65 percent / 3-chloroperbenzoic acid / CH2Cl2 / 2 h / Ambient temperature
6: 73 percent / lithium aluminium hydride, (S)-(-)-binaphthol / ethanol; tetrahydrofuran / 1.5 h
7: 55 percent / NaBH4 / CH2Cl2; ethanol / 1 h / Ambient temperature
8: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, 20 min
9: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 1.5 h / 2068.6 Torr
10: 90 percent / potassium carbonate / acetone / 42 h / 56 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; bromine; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium acetate; copper; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00097a005