Multi-step reaction with 10 steps
1.1: Et3N / 1 h / 25 °C
2.1: NaOMe / methanol / 1 h / 25 °C
2.2: 8.5 g / LiAlH4 / tetrahydrofuran / 30 h / 24 °C
3.1: 9.5 g / iPr2NEt; AgNO3 / CH2Cl2 / -78 - 25 °C
4.1: H2 / Pd(OH)2/C / ethanol / 48 h / 25 °C / 4500.36 Torr
5.1: 16.0 g / pyridine / 25 °C
6.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.75 h / 60 °C
6.2: Et3SiOTf / benzene / 1.5 h / 45 °C
7.1: 9.13 g / Et4NF*2H2O; AcOH / acetonitrile / 0.33 h / 25 °C
8.1: AgNO3 / CH2Cl2 / 0.5 h / 25 °C
9.1: NaNO2 / dimethylsulfoxide / 4 h / 75 °C
10.1: 2.17 g / NaOH; water / tetrahydrofuran; methanol / 0.13 h / 4 °C
With
pyridine; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; water; hydrogen; sodium methylate; tetraethylammonium fluoride; silver nitrate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite;
palladium dihydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U