Multi-step reaction with 7 steps
1: 82 g / 1a) ozone, 1b) dimethylsulphide / CH2Cl2; methanol / 1a) -78 deg C, 6 h, 1b) r.t., 3 h
2: 81 percent / hydroxylamine hydrochloride, triethylamine / methanol / 17 h
3: 1) n-butyllithium / 1) THF, hexane, -78 deg C -> 0 deg C, 2) THF, -78 deg C
4: pyridine-borane complex, 10percent aqueous hydrochloric acid / ethanol / Ambient temperature
5: 1) sodium methoxide / 1) MeOH, reflux, 2) r.t.
6: 1) trifluoroacetic anhydride, dimethylsulphoxide, 2) ethyldiisopropylamine / 1) CH2Cl2, -78 deg C
7: methanol
With
hydrogenchloride; n-butyllithium; dimethylsulfide; hydroxylamine hydrochloride; sodium methylate; borane pyridine complex; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride;
In
methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)88493-3