Multi-step reaction with 7 steps
1: 72 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature
2: 1) lithium di-isopropylamide, 2) hexamethylphosphoric triamide / 1) oxolane, -76 deg C, 1 h, 2) 5 h
3: 64 percent / hydroxylamine hydrochloride, NaCO3 / ethanol / 20 h / Heating
4: 30 percent / LiALH4 / tetrahydrofuran / 4 h / 100 °C
5: 70 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodi-imide / CH2Cl2 / 2 h / Ambient temperature
6: 1) NaH / 1) DMF, r.t., 1 h, 2) 20 min
7: 80 percent / aq. 70percent acetic acid / 7.5 h / 80 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; sodium hydride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/0008-6215(90)80164-X