Acetic Acid → 3-(p-Chlorobenzylamino)propyl(n-butyl)phosphinic acid ethyl ester
Reaction equation
[CH2:1]([O:3][P:4]([CH2:10][CH2:11][CH2:12][NH2:13])([CH2:6][CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][P:4]([CH2:10][CH2:11][CH2:12][NH:13][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=1)([CH2:6][CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2]Participants
Procedure
4.14 g of 3-aminopropyl(n-butyl)phosphinic acid ethyl ester are mixed with 2.51 g of p-chlorobenzaldehyde, and first 1.2 g of glacial acetic acid and then a solution of 0.42 g of sodium cyanoborohydride in 5 ml of methanol are added, whereupon an exothermic reaction takes place. The mixture is then stirred at room temperature for 2.5 hours and adjusted to pH 8, and the volatile constituents are removed under reduced pressure. The residue is dissolved in dichloromethane, washed with water, dried over sodium sulfate and concentrated by evaporation. The residue is purified by chromatography on silic gel, yielding 3-(p-chlorobenzylamino)propyl(n-butyl)phosphinic acid ethyl ester; 1H--NMR spectrum (in CDCl3): δ=7.30-7.32 (4H,m); 4.02 (2H,q); 3.74 (2H,s); 2.67 (2H,t); 2.5-2.2 (1H,S); 1.79-1.64 (6H,m); 1.53 (2H,m); 1.42 (2H,m); 1.31 (3H,t); 0.81 (3H,t); 31P--NMR spectrum (in CDCl3); δ=58.16.
Workup
- customthe volatile constituents are removed under reduced pressure
- dissolutionThe residue is dissolved in dichloromethane
- washwashed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated by evaporation
- customThe residue is purified by chromatography on silic gel
Sources & evidence
- ORD record
- ord-54056f2c33f54be2ae20168cf5cd40c2
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05545631
Reaction notes
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