Multi-step reaction with 13 steps
1: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, 3 h
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 5 min, 2.) CH2Cl2, RT, 1 h
3: 1.) nBuLi / 1.) THF, -23 deg C, 1 h, 2.) THF, a) -78 deg C, 30 min, b) 0 deg C, 45 min
4: 99 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h
5: 97 percent / PPh3, CBr4 / tetrahydrofuran / 0.5 h / Ambient temperature
6: 1.) Mg, 1,2-dibromoethane, 2.) CuBr*Me2S / 1.) Et2O, 160 min, 2.) THF, Et2O, -23 deg C, 140 min
7: 1.) N-methylmorpholine, 2.) 1-hydroxybenzotriazole, 3.) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide
8: aq. LiOH / tetrahydrofuran; methanol / 2 h / Ambient temperature
9: H2 / 10percent Pd/C / tetrahydrofuran / 13.5 h
10: 4-(dimethylamino)pyridine, benzotrazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate / dimethylformamide / 96 h / 25 °C
11: 51 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature
12: Dess-Martin periodinane / CH2Cl2 / 1 h
13: <3H>NaBH4 / tetrahydrofuran / 1 h / 0 °C
With
4-methyl-morpholine; dmap; lithium hydroxide; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; <3H>NaBH4; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; Dess-Martin periodane; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; ethylene dibromide; triethylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ja9615841