Multi-step reaction with 8 steps
1: 1) i-BuOCOCl, NMM / 1) CH2Cl2, -60 deg C
2: HCl / dioxane; acetic acid
3: 81 percent / NaBH4, 3 Angstroem molecular sieve / methanol
4: 1) Me3Al / 1) hexane, ClCH2CH2Cl, r.t., 1 h, 2) ClCH2CH2Cl, 83 deg C, 36 h
5: 75 percent / pyridinium chlorochromate / CH2Cl2 / 12 h / Ambient temperature
6: 91 percent / K2CO3 / methanol / 12 h / Ambient temperature
7: 76 percent / 8 N Jones reagent / acetone / 2 h / 0 - 5 °C
8: 1) Et3N, i-BuO2CCl, 2) hydroxylamine hydrochloride, Et3N / 1) THF, r.t., 1 h, 2) r.t., 12 h
With
4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; jones reagent; 3 A molecular sieve; hydroxylamine hydrochloride; trimethylaluminum; potassium carbonate; triethylamine; pyridinium chlorochromate; isobutyl chloroformate;
In
1,4-dioxane; methanol; dichloromethane; acetic acid; acetone;
DOI:10.1016/S0040-4020(01)90212-1