反応 #417897

反応方程式

C9H19N3

BH3.THF

compound 2

1-cyano-cyclobutyl carboxylic acid (2-amino-ethyl) amide

→

N′-((1-(amino methyl)-cyclobutyl)methyl) ethane-1,2-diamine

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度the mixture gradually warmed up
2. 2
   温度to reflux for 36 h
3. 3
   その他Then the solution was evaporated
4. 4
   workup.DISSOLUTIONthe residue dissolved in C2H5OH (100 mL)
5. 5
   温度6N HCl (10 mL), and the resulting solution refluxed for 12 h
6. 6
   その他The solution was evaporated
7. 7
   workup.DISSOLUTIONthe residue dissolved in 20 mL of distilled water
8. 8
   洗浄The column was eluted first with H2O
9. 9
   workup.ADDITIONThe 3.5-4 N HCl solution containing the product
10. 10
    その他was evaporated to dryness
11. 11
    その他yielding 2.98 g (50.0%)

実験手順

To compound 2 (5.37 g, 0.083 mol) under N2, tetrahydrofuran (THF, 50 ml) was added by syringe. The mixture was cooled to −5 to 0° C., 1M BH3.THF (50 ml) added by syringe, and then the mixture gradually warmed up and brought to reflux for 36 h. Then the solution was evaporated, the residue dissolved in C2H5OH (100 mL) and 6N HCl (10 mL), and the resulting solution refluxed for 12 h. The solution was evaporated, the residue dissolved in 20 mL of distilled water, acidulated with HCl to pH 2 and the solution applied to an AG 50W×8 cation exchange resin column (200-400 mesh, H+ form, 100 mL of resin, 3.0 cm column diameter). The column was eluted first with H2O and then with a gradient HCl. The 3.5-4 N HCl solution containing the product was evaporated to dryness, yielding 2.98 g (50.0%). MS (ESI): m/z: 158.23 [M+H]+. Anal. Calcd (Found) for C9H19N3: C, 61.10 (60.83); H, 12.18 (12.41); N, 26.72 (26.36). 1H NMR (D2O, 400 MHz), δ (ppm): 3.39-3.33 (m, 4H, —NHCH2CH2NH2), 3.25 (s, 2H, —NH2CH2CCH2NH—), 3.16 (s, 2H, —NH2CH2CCH2NH—), 1.95-1.86 (m, 6H, —CCH2CH2CH2—). 13C NMR (D2O, 400 MHz), δ (ppm): 52.73, 45.51, 43.64, 38.32, 35.50, 26.64, 14.16.

出典