Multi-step reaction with 11 steps
1: 1) activated Zn powder, I2 / 1) THF, rt, ultrasonication, 2) THF, 35 min, ultrasonication
2: NH3 / diethyl ether / -78 deg C to rt
3: BH3*Me2S / tetrahydrofuran / Heating
4: Et3N / tetrahydrofuran / 0 °C
5: SnCl2 / ethanol / Heating
7: H2 / Pd/C / ethanol
8: iBuOCOCl, NMM / MeCN, -20 deg C
9: TFA / 0 °C
10: tetrahydrofuran / 40 °C
11: 1) Pd/C, 3 Angstroem molecular sieves, AcOH, 2) H2, Pd/C, AcOH, HCl / 1) CH2Cl2, 2) iPrOH
With
4-methyl-morpholine; hydrogenchloride; palladium on activated charcoal; dimethylsulfide borane complex; 3 A molecular sieve; ammonia; hydrogen; iodine; acetic acid; triethylamine; trifluoroacetic acid; tin(ll) chloride; zinc; isobutyl chloroformate;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol;
DOI:10.1016/0040-4039(91)80491-N