Multi-step reaction with 7 steps
1: 80 percent / piperidine, acetic acid / benzene / 28 h / Heating
2: 98 percent / tetramethylguanidine / 2 h / -20 °C
3: 64 percent / ammonium formate / 10percent Pd/C / methanol / 0.5 h / Ambient temperature
4: 98 percent / titanium trichloride, sodium acetate / H2O; methanol / 2 h
5: calcium chloride, sodium borohydride / methanol / 4 h
6: pyridine / 1.) 0 deg C, 1 h, 2.) from 0 deg C to RT, 3 h
7: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1.) RT, 1 h, 2.) from RT to 100 deg C, 6 h
With
piperidine; pyridine; sodium tetrahydroborate; titanium(III) chloride; 1,1,3,3-tetramethylguanidine; sodium acetate; ammonium formate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium chloride;
palladium on activated charcoal;
In
methanol; water; benzene;
DOI:10.1021/jm00060a012