Benzylamine → N-[5-((1R)-2-Benzylamino-1-triethylsilanyloxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamide

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Reaction Conditions

Reaction Steps

N-[2-benzyloxy-5-((1R)-2-iodo-1-triethylsilanyloxy-ethyl)-phenyl]-methanesulfonamide (0.56 g, 1 mmol) was dissolved in benzylamine (0.54 g, 5 mmol) and stirred at 65° C. for 22 h. The mixture was then cooled to room temperature, and stirred with hexanes. The hexanes solution was filtered through a pad of silica gel, and the residue was stirred with ether (10 ml). The ether solution was diluted with 10 ml of hexanes, and passed through the silica gel pad. The filter pad was eluted with ether-hexanes (1:1 to 3:1), and the filtrate was evaporated. The residue was washed with isooctane to give 0.44 g of a colorless gum; MS (ES) m/z 541.1 (MH+); HRMS (EI) Calcd. for C29H40N2O4SSi (M+): 540.2478, Found: 540.2472.

Provenance & Evidence