Multi-step reaction with 8 steps
1: N-methylmorpholine / tetrahydrofuran / 0.33 h / -20 °C
2: tetrahydrofuran; dimethylformamide / 0.5 h
3: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C
4: CeCl3*7H2O, NaBH4 / methanol / 0.5 h / Ambient temperature
5: diisopropylethylamine / CH2Cl2 / 1 h / 0 °C
6: 1.) CuCN / 1.) THF, a) -70 deg C, 20 min, b) 0 deg C, 30 min, 2.) THF, -70 deg C, 60 min
7: MCPBA / CH2Cl2 / 7 h / 0 °C
8: NaN3, NH4Cl / dimethylformamide; H2O / a) 85 deg C, 3 h, b) RT, overnight
With
4-methyl-morpholine; sodium tetrahydroborate; sodium azide; cerium(III) chloride; ammonium chloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm970081i