Formaldehyde → HCID 18504545, compound

HRID 1463770Notes

Reaction equation

HRID 1463770 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].C=O.[C:21]([BH3-])#N.[Na+]>O>[CH3:21][N:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:18][CH:17]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19023162HCID 19023162, compound

Product 1

HCID 18504545HCID 18504545, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-758f26cffeb6474498269036e5ce2622
Source dataset
uspto-grants-1994_04
Patent number
US05302516

Reaction notes

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