Synthesis and reactions of organic compounds with a nitrogen atom .12. Toluenesulfonamidation of (+)-2-carene and synthesis of amines and aminoalcohols of the carane group
Toluenesulfonamidation of (+)-2-carene 2 afforded: 4-methyl-N-trans-(2-caren-4-yl) benzenesulfonamide 3 and 4-methyl-N-(2-caren-10-yl)benzenesulfonamide 4, which were converted by the reduction with sodium in liquid ammonia to: (-)-trans-4-amino-2-carene 5 and (+)-10-amino-2-carene 6. Hydroboration-oxidation of amines 5 and 6 afforded aminoalcohols 7, 8 and 9.