Multi-step reaction with 10 steps
1: 94 percent / 80percent m-chloroperbenzoic acid / CHCl3 / 6 h / Ambient temperature
2: 1.) LiAlH4, 2.) 10percent aq. NaOH / 1.) ether, 16h, RT, 2.) RT, 7h
3: 58 percent / pyridinium dichromate / CH2Cl2 / 8 h / Ambient temperature
4: pentane / 8 h / Ambient temperature; Irradiation
5: 1.) LiAlH4, 2.) 2N HCl / 1.) ether, 8h, RT, 2.) 8h, RT
6: 94 percent / methanol / 24 h / Ambient temperature
7: 62 percent / Florisil (60-100 mesh) / ethyl acetate / 20 h / 80 °C
8: 100 percent / sodium borohydride / aq. ethanol / 0.42 h / -45 °C
9: 96 percent / H2 / 10percent Pd-C / methanol / 1 h / 760 Torr / Ambient temperature
10: 1.) 60percent sodium hydride / 1.) DMSO, RT, 30 min, 2.) 65 deg C, DMSO, 1.5h then 30 deg C
With
hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; Florisil; hydrogen; sodium hydride; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; chloroform; ethyl acetate; pentane;
DOI:10.1016/S0040-4020(01)87735-8