Multi-step reaction with 10 steps
1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 2.5 h, 2.) a) 0 deg C, 0.5 h, b) RT, 2.5 h
2: 1.) n-BuLi / 1.) Et2O, TMEDA, hexane, 0 deg C, 1 h, 2.) from 0 deg C to RT
3: (COCl)2, DMF / CH2Cl2 / 1 h / 0 °C
4: CH2Cl2 / 1.5 h / 0 °C
5: 83 percent / K2CO3 / acetone / 12 h / Heating
6: 88 percent / 0.25 h
7: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) from 0 deg C to RT, 1 h
8: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C, 2.) from -78 deg C to 0 deg C
9: 32 percent / diethylaminosulfur triflupride / CH2Cl2 / 5.25 h
10: 91 percent / H2 / 10percent Pd/C / methanol / 2 h / Ambient temperature
With
sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; diethylamino-sulfur trifluoride; hydrogen; sodium hydride; potassium carbonate; ozone; N,N-dimethyl-formamide;
palladium on activated charcoal;
In
methanol; dichloromethane; acetone;
DOI:10.1021/jm00109a013