Multi-step reaction with 8 steps
1: sodium hydride / tetrahydrofuran; dimethylformamide / 1 h / 0 °C
2: methanol / Ambient temperature
3: 95 percent / pyridine / CH2Cl2 / 1 h / 0 °C
4: 66 percent / 1) sodium azide, ceric ammonium nitrate, 2) sodium nitrite / 1) acetonitrile, -20 deg C, 2) 1,4-dioxane, 3 h, 80 deg C
5: 79 percent / 1,8-diazabicylo<5.4.0>undec-7-ene / 1,2-dichloro-ethane / 2 h / Ambient temperature
6: 55 percent / activated powdered 4 Angstroem molecular sieve, BF3*OEt2 / toluene; CH2Cl2 / 4 h / -20 °C
7: 73 percent / pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature
8: 78 percent / 24 h / Ambient temperature
With
pyridine; methanol; dipyridinium dichromate; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite;
In
tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(90)84259-W