반응 #1550952

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N-(p-nitrobenzyl)δ-aminovaleric acid

formaldehyde

sodium cyanoborohydride

→

product

수율 85.0%

N-methyl-N-(p-nitrobenzyl)δ-aminovaleric acid

수율 85.0%

용매

water

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후처리

1. 1
   기타After quenching with 6 ml of 1 M hydrochloric acid the solution
2. 2
   세척The column was subsequently washed with 150 ml water
3. 3
   세척the product eluted with 0.7 M ammonia
4. 4
   기타After evaporation
5. 5
   기타the remaining oil was further purified by silicagel chromatography (1×15 cm, methanol:dichloromethane=1:1)
6. 6
   workup.ADDITIONThe product containing fractions (Rf =0.22)
7. 7
   기타were collected
8. 8
   기타the solvent removed in vacuo

실험 절차

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.

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