Multi-step reaction with 7 steps
1: 85 percent / LiAlH4 / tetrahydrofuran; diethyl ether / a) RT, 1 h, b) reflux, 1.5 h
2: 37 percent / 4-(dimethylamino)pyridine / dimethylformamide; tetrahydrofuran / 1 h / Ambient temperature
3: 85 percent / PCC, Celite / CH2Cl2 / 1.5 h / Ambient temperature
4: 87 percent / tetrahydrofuran; cyclohexane; diethyl ether / -78 - 20 °C
5: 1.) 9-BBN, 2.) 6 N aq. NaOH, 30percent aq. H2O2 / 1.) THF, from 0 deg C to RT, 4 h, 2.) THF, ethanol, 50 deg C, 1 h
6: 96 percent / 4-(dimethylamino)pyridine / dimethylformamide; tetrahydrofuran / 1 h / Ambient temperature
7: 1.) t-BuLi / 1.) THF, pentane, -78 deg C, 30 min, 2.) THF, pentane, -78 deg C, 2 h
With
dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; tert.-butyl lithium; pyridinium chlorochromate;
In
tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1021/jm00022a019