반응 #78375

반응 방정식

tert-Butyl-4-nitrophenyl carbonate

DMF

ethylenediamine

DMF

→

product

수율 63.0%

Mono-Boc-ethylenediamine

수율 63.0%

반응 조건

후처리

1. 1
   기타The mixture was evaporated to dryness, in vacuo
2. 2
   workup.DISSOLUTIONthe resulting oil dissolved in water (250 ml)
3. 3
   여과The solution then was filtered
4. 4
   추출extracted with chloroform (3×250 ml)
5. 5
   기타was adjusted to 12 at 0° C. with 2 M sodium hydroxide
6. 6
   추출the aqueous solution extracted with methylene chloride (3×300 ml)
7. 7
   건조After treatment with sat. aqueous sodium chloride (250 ml), the methylene chloride solution was dried over magnesium sulfate
8. 8
   여과After filtration
9. 9
   기타the solution was evaporated to dryness, in vacuo

실험 절차

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 4 M hydrochloric acid. The solution then was 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 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): δ1.44 (s, 9H); 2.87 (t, 2H); 3.1 (q, 2H); 5.62 (s, broad).

출처