Hexamethylenediamine → N-BOC-1,6-diaminohexane

Participants

Reaction Steps

A solution of 1,6-diaminohexane (14 g, 0.12 mol) in ethanol (500 mL) was mixed with a solution of di-t-butyl carbonate (23 g, 0.1 mol) in ethanol (500 mL) and stirred overnight. The mixture was filtered, concentrated and the residue was shaken with a mixture of ether (200 mL) and water (50 mL). The aqueous phase was extracted twice with ether (50 mL) and the organic phase was extracted sequentially with brine, cold 0.4N hydrochloric acid (150 mL) and water (2×100 mL). The pH of the acidic extract was brought to 12-13 with 1N sodium hydroxide and it was extracted twice with ether (50 mL). The organic phase was washed with brine, dried (sodium sulfate) and concentrated to yield the title compound (13.16 g, 49%). TLC Rf 0.53 (Kieselgel 60 F254, 15:3:2 2-butanol:formic acid:water); MS(ES) m/e 217.0; 1NMR (400 MHz, CDCl3): δ4.57 (br s, 1H), 3.10-3.12 (m 2H), 2.68-2.71 (m 2H), 1.84 (br s 2H), 1.44-1.48 (br s 9H), 1.32-1.34 (br s 8H).

Provenance & Evidence