Multi-step reaction with 8 steps
1: 82 percent / Ph3P, NBS / CH2Cl2 / 3.5 h
2: 84 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 1,5 h, 2.) -78 deg C, 10 h
3: LiAlH4 / diethyl ether / Ambient temperature
4: 88 percent / imidazole / dimethylformamide / 12 h / 45 °C
5: 88 percent / n-BuLi, LiBr / hexane; tetrahydrofuran / 1.) -78 deg C, 1 h; -78 deg C to -40 deg C, 15 min, 2.) -78 deg C to 0 deg C, 12 h
6: 92 percent / LiAlH4 / tetrahydrofuran / 6 h / 45 °C
7: 1.) DMSO, (COCl2)2, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 35 min, 2.) -78 deg C to r.t., 4 h
8: 94 percent / hydroxylamine hydrochloride, aq. Na2CO3 / diethyl ether / 26 h
With
1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; (COCl2)2; hydroxylamine hydrochloride; sodium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium bromide; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00127a028