Multi-step reaction with 11 steps
1: 75 percent / pyridine / CH2Cl2 / 2 h / -40 °C
2: 36 percent / Et3N, DMAP / CH2Cl2 / 25 °C
3: tetrabutylammonium nitrate / dimethylformamide / 16 h / 100 °C
4: hydrogen / 10 percent Pd-C / methanol / 2.5 h / 25 °C / 2844.3 Torr
5: tetrazole / CH2Cl2 / 25 °C
6: m-chlorperbenzoic acid / CH2Cl2 / 0 °C
7: NH3 / methanol / 36 h / 25 °C
8: 57 percent / silver triflate, tetramethylurea, molecular sieves 4 Angstroem / CH2Cl2 / 24 h / 25 °C
9: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C
10: 90 percent / hydrogen / 10 percent Pd-C / methanol; H2O / 18 h / 25 °C
11: 86 percent / aq. acetic acid / 2.5 h / 80 °C
With
pyridine; 1H-tetrazole; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; hydrogen; silver trifluoromethanesulfonate; tetrabutylammonium nitrate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetramethylurea;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(91)80003-K