Borane;tetrahydrofuran → HCID 58193747, compound

Temperature

-2.5 °C

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.

1. temperaturethe mixture gradually warmed up
2. temperatureto reflux for 36 h
3. customThen the solution was evaporated
4. dissolutionthe residue dissolved in C2H5OH (100 mL)
5. temperature6N HCl (10 mL), and the resulting solution refluxed for 12 h
6. customThe solution was evaporated
7. dissolutionthe residue dissolved in 20 mL of distilled water
8. washThe column was eluted first with H2O
9. additionThe 3.5-4 N HCl solution containing the product
10. customwas evaporated to dryness
11. customyielding 2.98 g (50.0%)

ORD record

ord-adf9f4c612bc452fb1b7ef927b2a574a

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877163B2