Multi-step reaction with 26 steps
1: 41 g / tetraethylammonium chloride, aq. potassium fluoride dihydrate / acetonitrile; H2O / 6 h / Ambient temperature
2: 88 percent / pyridine / 16 h / 0 °C
3: 80 g / methanolic sodium methoxide / tetrahydrofuran; methanol / 1 h / Ambient temperature
4: 75 percent / pyridine / CH2Cl2 / 9 h / 0 °C
5: 84 percent / tetrabutylammonium hydrogen sulphate, aq. sodium hydroxide / toluene / -15 - -10 °C
6: 80 percent / methanolic sodium methoxide / CH2Cl2; methanol / 72 h / 0 °C
7: 88 percent / sodium hydride, tetrabutylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature
8: 71 percent / sodium azide, ammonium chloride / aq. ethanol / 11 h / 80 - 90 °C
9: 1.) acetic anhydride, aq. sodium acetate 2.) sodium borohydride / 1.) DMSO a) 12 h, RT. b) 3 h, 0 deg C 2.) dichloromethane-ethanol-water, 0 deg C, 30 min
10: 1.) lithium aluminium hydride, water, aq. sodium hydroxide 2.) saturated aq. sodium hydrogen carbonate / 1.) diethyl ether, RT, 2 h 2.) THF-methanol, 0 deg C, 2 h
11: 2.1 g / DMAP, pyridine / acetonitrile / 2 h / Ambient temperature
12: 96 percent / tributyltin hydride, AIBN / toluene / 1.5 h / 80 °C
13: 88 percent / acetic acid, water / 2 h / 60 - 70 °C
14: 62 percent / pyridine / 60 h / Ambient temperature
15: 91 percent / sodium azide / dimethylformamide / 22 h / 100 °C
16: 74 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / Ambient temperature
17: 1.) zinc iodide, aq. sodium hydrogen carbonate 2.) saturated aq. sodium hydrogen carbonate / 1.) 1,2-dichloroethane 2.) THF-methanol, 0 deg C, 1 h
18: 85 percent
19: lithium iodide
20: DBU
21: 1.) mercury(II) chloride 2.) methanesulphonyl chloride, pyridine / 1.) acetone-water, RT, 3 d 2.) a) -15 deg C b) RT
22: 1.) cerium(III) chloride heptahydrate, sodium borohydride 2.) TPP, hydrazoic acid, DEAD
23: potassium azodicarboxylate-acetic acid / acetonitrile / 3 h / Ambient temperature
24: DDQ / CH2Cl2; H2O / 3 h / Ambient temperature
25: 1.) DMSO-TFAA, triethylamine 2.) acetic acid, sodium cyanoborohydride
26: 75 percent / H2 / 10percent palladium on carbon / methanol; HCl / 33 h / Ambient temperature
With
pyridine; dmap; potassium fluoride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen azide; sodium azide; cerium(III) chloride; barium hydroxide octahydrate; 2,2'-azobis(isobutyronitrile); ammonium chloride; tetraethylammonium chloride; water; hydrogen; tri-n-butyl-tin hydride; sodium methylate; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; potassium diazodicarboxylate; acetic anhydride; thiamine diphosphate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dichloride; zinc(II) iodide; barium(II) oxide; lithium iodide; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; hydrogenchloride; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;