Ethanol → N-BOC-1,6-diaminohexane

Participants

Reaction Steps

Tert-butylphenyl carbonate (6.37 mL, 14.7 mmol) was added dropwise to a solution of 1,6 diaminohexane (4 g, 14.7 mmol) in ethanol (20 mL) at 80° C. The reaction mixture was refluxed overnight. The reaction mixture was then cooled to room temperature leaving a yellow solution. The solution was concentrated to 15 mL and diluted with water (30 mL). The solution pH was adjusted to 3 with 2M HCl followed by an extraction with dichloromethane (3×50 mL). The water solution pH was then adjusted to pH 12 followed by extraction with dichloromethane (3×50 mL). The organic solutions were combined, washed with sodium bicarbonate (2×50 mL), dried with sodium sulfate, and concentrated to a yellow oil. Characterization matched previously published values (M. Pittelkow, et al., “Mono Carbamate Protection of Aliphatic Diamines Using Alkyl Phenyl Carbonates,” Organic Syntheses (2007) 84, pg 207).

Provenance & Evidence