Ethanol → N-BOC-1,6-diaminohexane

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).

1. temperatureThe reaction mixture was refluxed overnight
2. customleaving a yellow solution
3. concentrationThe solution was concentrated to 15 mL
4. additiondiluted with water (30 mL)
5. extractionfollowed by an extraction with dichloromethane (3×50 mL)
6. extractionfollowed by extraction with dichloromethane (3×50 mL)
7. washwashed with sodium bicarbonate (2×50 mL)
8. dry with materialdried with sodium sulfate
9. concentrationconcentrated to a yellow oil

ORD record

ord-3968b3c5cd24426a97970061fbf8b2fa

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921426B2