Multi-step reaction with 9 steps
1: 2.) acetyl chloride / 1.) camphorsulfonic acid / 1.) DMF, 80 deg C, 4 h, 2.) CH2Cl2, MeOH, 23 deg C, 1 h
2: 96 percent / NaH / dimethylformamide / 1.) ice bath temp., 3 h, 2.) 8-10 deg C, then r.t., 3 h
3: 100 percent / aq. conc. HCl / methanol / 21 h / Ambient temperature
4: 1.) di-n-butyltin oxide / 1.) MeOH, reflux, 2 h, 2.) DMF, toluene, ice bath, 1 h
5: 98 percent / NaH / dimethylformamide / 5 h / Ambient temperature
6: 94 percent / aq. HCl / methanol / 5 h / Heating
7: 97 percent / diisopropylammonium tetrazolide / CH2Cl2 / 20 h / Ambient temperature
8: 79 percent / tetrazole / CH2Cl2; acetonitrile / 1.) r.t., 5 h, 2.) 35 - 40 deg C, 64 h
9: 98 percent / t-BuOOH / CH2Cl2 / 1.) ice bath, 90 min, 2.) r.t., 20 min
With
1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; N,N-diisopropylamine tetrazolide; sodium hydride; di(n-butyl)tin oxide; acetyl chloride;
hydrogenchloride; camphor-10-sulfonic acid;
In
methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00084a010