Ethylenediamine → N-BOC-ethylenediamine

Temperature

0 °C

tert-Butyl-4-nitrophenyl carbonate (1, 10 g, 0.0418 mol) dissolved in DMF (50 mL) was added dropwise over a period of 30 minutes to a solution of ethylenediamine (27.9 mL, 0.418 mol) and DMF (50 mL) and stirred overnight. The mixture was evaporated to dryness in vacuo, and the resulting oil dissolved in water (250 mL). After cooling to 0° C., the pH was adjusted to 3.5 with 4 M hydrochloric acid. The solution was then filtered and extracted with chloroform (3×250 mL). The pH was adjusted to 12 (at 0° C.) with 2 M sodium hydroxide, and the aqueous solution extracted with methylene chloride (3×300 mL). After treatment with a solution of saturated aqueous sodium chloride (250 mL), the methylene chloride solution was dried over magnesium sulfate. After filtration, the solution was evaporated to dryness in vacuo, resulting in 4.22 g (63%) of the product as an oil. 1H-NMR (90 MHz, CDCl3) δ: 1.44 (s, 9H); 2.87 (t, 2H); 3.1 (q, 2H); 5.62 (sb).

1. customThe mixture was evaporated to dryness in vacuo
2. dissolutionthe resulting oil dissolved in water (250 mL)
3. filtrationThe solution was then filtered
4. extractionextracted with chloroform (3×250 mL)
5. customwas adjusted to 12 (at 0° C.) with 2 M sodium hydroxide
6. extractionthe aqueous solution extracted with methylene chloride (3×300 mL)
7. dry with materialAfter treatment with a solution of saturated aqueous sodium chloride (250 mL), the methylene chloride solution was dried over magnesium sulfate
8. filtrationAfter filtration
9. customthe solution was evaporated to dryness in vacuo

ORD record

ord-b504b5288c9849d68ade556358fc1aec

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613873B1