Multi-step reaction with 12 steps
1: BOP-Cl, Et3N / CH2Cl2 / 80 h / 25 °C
2: 97 percent / 2,6-lutidine / CH2Cl2 / 0 deg C, 15 min; 25 deg C, 15 min
3: 90 percent / H2 / Pd/C / methanol / 2 h
4: 98 percent / DMAP, isopropenyl chloroformate / CH2Cl2 / 2 h / -5 °C
5: 97 percent / acetonitrile / 2.5 h / Heating
6: 73 percent / NaBH4 / acetic acid; CH2Cl2 / 4.5 h / 0 °C
7: Et3N / CH2Cl2 / 1 h / 25 °C
8: 1,8-diazabicyclo<5.4.0>undec-7-ene, Et3N / CH2Cl2 / 0.33 h
9: 97 percent / 4N HCl / dioxane / 2 h / 0 °C
10: 50 percent / BOP-Cl, Et3N / CH2Cl2 / 25 °C
11: 98 percent / 4N HCl / dioxane / 4 h / 0 °C
12: 56 percent / BOP-Cl, Et3N / CH2Cl2 / 25 °C
With
2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; Isopropenyl chloroformate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
palladium on activated charcoal;
In
1,4-dioxane; methanol; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/jo952123l