Reaction #417897

Reaction equation

C9H19N3

BH3.THF

compound 2

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

→

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

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturethe mixture gradually warmed up
2. 2
   Temperatureto reflux for 36 h
3. 3
   OtherThen the solution was evaporated
4. 4
   workup.DISSOLUTIONthe residue dissolved in C2H5OH (100 mL)
5. 5
   Temperature6N HCl (10 mL), and the resulting solution refluxed for 12 h
6. 6
   OtherThe solution was evaporated
7. 7
   workup.DISSOLUTIONthe residue dissolved in 20 mL of distilled water
8. 8
   WashThe column was eluted first with H2O
9. 9
   workup.ADDITIONThe 3.5-4 N HCl solution containing the product
10. 10
    Otherwas evaporated to dryness
11. 11
    Otheryielding 2.98 g (50.0%)

Procedure

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.

Source