Multi-step reaction with 7 steps
1: (-)-(1S,2R)-N,N-dibutylnorephedrine / hexane; toluene / 72 h / 0 °C
2: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
3: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
4: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
5: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
6: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
7: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
With
2,6-dimethylpyridine; dmap; lithium hydroxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; diisobutylaluminium hydride; (1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja974010k