Ethylenediamine → N-BOC-ethylenediamine

Temperature

0 °C

tert-Butyl-4-nitrophenyl carbonate (1) (10.0 g; 0.0418 mol) dissolved in DMF (50 ml) was added dropwise over a period of 30 min 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., pH was adjusted to 3.5 with 4M hydrochloric acid. The solution then was filtered and extracted with chloroform (3×250 ml). The pH was adjusted to 12 at 0° C. with 2M sodium hydroxide, and the aqueous solution extracted with methylene chloride (3×300 ml). After treatment with sat. 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 (oil). 1H-NMR (90 MHz; CDCl3): 61.44 (s, 9H); 2.87 (t, 2H); 3.1 (q, 2H); 5.62 (s, broad).

1. customThe mixture was evaporated to dryness, in vacuo
2. dissolutionthe resulting oil dissolved in water (250 ml)
3. filtrationThe solution then was filtered
4. extractionextracted with chloroform (3×250 ml)
5. customwas adjusted to 12 at 0° C. with 2M sodium hydroxide
6. extractionthe aqueous solution extracted with methylene chloride (3×300 ml)
7. dry with materialAfter treatment with sat. 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-e0cc1e8b96f94c02819e4721971b09d2

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05539082