Multi-step reaction with 11 steps
2: 92 percent / diisopropylethylamine / CH2Cl2 / Ambient temperature
3: 95 percent / NaH / tetrahydrofuran / -30 °C
4: 87 percent / NH3 / methanol
5: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr
6: 65 percent / HCl / methanol / 12 h / 50 °C
7: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature
8: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h
9: 30 percent / MCPBA, NaHCO3 / not given
10: 1.) Li, ClPPh2 / 1.) THF; 2.) THF
11: 1.) NaBH4; 2.) silica gel / 1.) EtOH, 0 degC, 3 h; 2.) room temperature, 30 min, benzene
With
hydrogenchloride; sodium tetrahydroborate; molecular sieve; tributyl-amine; potassium tert-butylate; ammonia; silica gel; lithium; sodium hydride; sodium hydrogencarbonate; chloro-diphenylphosphine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate;
palladium diacetate;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)87534-7