Multi-step reaction with 7 steps
1.1: dmap; triethylamine / dichloromethane / 20 °C
2.1: dmap; triethylamine / dichloromethane / 18.16 h / 24 °C
3.1: lithium triethylborohydride / toluene; tetrahydrofuran / 1.08 h / -50 - -45 °C
3.2: 14.42 h / -50 - 20 °C
3.3: 0.08 h / Cooling with ice/water
4.1: diethylzinc / toluene / 0.25 h / -30 °C
4.2: 19.66 h / -25 - -21 °C
4.3: 0.33 h / -25 - 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.83 h / 20 °C
6.1: sodium periodate; ruthenium trichloride / tetrachloromethane; acetonitrile; water / 1.25 h
7.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 20 °C
7.2: 3 h / 140 °C / Sealed vessel
With
dmap; ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; diethylzinc; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;