Multi-step reaction with 7 steps
1: 60 percent / chlorosulfonyl isocyanate / CH2Cl2 / 0.75 h / Heating
2: 65 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.25 h / Heating; Irradiation
3: 90 percent / K2CO3 / acetone / Heating
4: 1.) BH3, 2.) 12 N HCl / 1.) THF, reflux, 1 h, 2.) reflux, 1 h
5: 25 percent / 1.) 2,6-lutidine / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) DMF, RT, 24 h
6: H2 / 10percent Pd/C / ethyl acetate / 22.5 h
7: 38 percent / 2,6-lutidine / CH2Cl2 / Ambient temperature
With
2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; Perbenzoic acid; isocyanate de chlorosulfonyle; borane; hydrogen; potassium carbonate;
palladium on activated charcoal;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; ethyl acetate; acetone;
DOI:10.1021/jm00171a018