(S)-3-AMINOPENTANENITRILE synthesis
- Product Name:(S)-3-AMINOPENTANENITRILE
- CAS Number:639804-64-1
- Molecular formula:C5H10N2
- Molecular Weight:98.15
Yield:400090-60-0 69.3%
Reaction Conditions:
Stage #1: 3-aminopentanenitrilewith Di-p-toluoyl-L-tartaric acid in ethanol; for 0.0833333 h;Heating / reflux;Resolution of racemate;
Stage #2: with sodium hydroxide in water;
Steps:
10 Example 10; Racemate resolution using (-)-di-O-p-toluyl-(L)-tartaric acid
1.50 g (15.3 mmol) of 3-aminopentanenitrile are dissolved in 15 ml of ethanol. 2.95 g (7.64 mmol) of (-)-di-O-p-toluyl-(L)-tartaric acid are added to this solution in one portion. The suspension is heated to boiling for 5 minutes. After cooling to 20 °C, the product forming as a solid is filtered off and dried at 40 °C under reduced pressure for 10 hours. The product is then dissolved in 20 ml of 1N sodium hydroxide solution. The aqueous phase is extracted twice with 10 ml each time of dichloromethane. The solvent of the combined organic phases is distilled off under reduced pressure. 1.04 g (69.3%) of (R)-3-aminopentanenitrile are obtained as a colourless liquid. The ee (R) value is 17.4%.
References:
EP1413565,2004,A2 Location in patent:Page 8
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