Formaldehyde → HCID 18504545, compound

Participants

Reaction Steps

To a solution of 300 mg (1.19 mmol) of N-(p-nitrobenzyl)δ-aminovaleric acid in 6 ml of water were added 450 μl of a 37% aqueous formaldehyde solution (6.1 mmol) and 123 mg of sodium cyanoborohydride (1.96 mmol). This mixture was stirred for 45 min at rt. After quenching with 6 ml of 1 M hydrochloric acid the solution was directly adsorbed on a Dowex 50 (H+ -form) ion exchange column (2×10 cm). The column was subsequently washed with 150 ml water and the product eluted with 0.7 M ammonia. After evaporation, the remaining oil was further purified by silicagel chromatography (1×15 cm, methanol:dichloromethane=1:1). The product containing fractions (Rf =0.22) were collected and the solvent removed in vacuo. 270 mg (85% of product in form of a colorless oil was isolated. Attempts at crystallization failed. 1H-NMR (200 MHz,D2O):8.10 (d,J =8.7/2H), 7.46 (d, J =8.7/2H), 3.83 (s/2H), 2.59 (m(t)/2H), 2.28 (s/3H), 2.03 (m(t)/2H), 1.49-1.39 (m/4H); 13C-NMR (50 MHz, d6 -DMSO): 175.3, 147.8, 146.4, 129.4, 123.3, 60.6, 56.6, 41.8, 34.1, 26.3, 22.5; FAB+-MS:267 (M+1)+. EA (C13H18N2O4. O.H2O) calc. C 55.26 H 7.06 N 9.91, found: C 55.34 H 6.88 N 9.89.

Provenance & Evidence