Multi-step reaction with 7 steps
1: 1) AgF, 2) H2 / 2) 10percent Pd/C / 1) pyridine, 40 h, 2) CH3OH-CH3CO2H, overnight
2: 1) N,N-diisopropylethylamine, 2) CH3ONa / 1) CH2Cl2, room temperature, overnight, 2) Na, CH3OH, room temperature, overnight
3: 98.1 percent / pyridinium chlorochromate / CH2Cl2 / Heating; molecular sieves 3A, overnight
4: pyridine / 1) room temperature, overnight, 2) room temperature, 2 days
5: 65.3 percent / LiAlH4 / diethyl ether / 2 h / Heating
6: 1) H2, 2) pyridine / 1) Ra-Ni W-4 / 1) CH3OH, 110 atm, room temperature, 3 days
7: 63.3 percent / ZnBr2 / CH2Cl2 / Ambient temperature; overnight
With
pyridine; lithium aluminium tetrahydride; hydrogen; sodium methylate; silver fluoride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; zinc dibromide;
palladium on activated charcoal; Ra-Ni W-4;
In
diethyl ether; dichloromethane;
DOI:10.1246/bcsj.57.2538