Multi-step reaction with 7 steps
1: SnCl4 / CH2Cl2 / 5 h / Ambient temperature
2: NaOMe / methanol / 14 h
3: 78 percent / p-TsOH*H2O / CH2Cl2; dimethylformamide / 16 h / Heating
4: 1.) NaH / 1.) DMF, 15 deg C, 30 min, 2.) DMF, RT, overnight
5: 83 percent / NaCNBH4, 3 A sieves, HCl(g) / tetrahydrofuran; diethyl ether / 0.92 h / 0 °C
6: 1.) 4 A sieves, AgOTf, sym-collidine / 1.) CH2Cl2, 30 min, 2.) CH2Cl2, RT, 60 h
7: 69 percent / NaOMe / methanol
With
2,4,6-trimethyl-pyridine; hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; tin(IV) chloride; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;