R-N-BENZYL-PROLINE

R-N-BENZYL-PROLINE Property

Boiling point:

343.1±35.0 °C(Predicted)

Density 

1.205±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.35±0.20(Predicted)

form 

solid

color 

White to light yellow

optical activity

31.9°(C=1.00g/100ml MEOH)

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

R-N-BENZYL-PROLINE Chemical Properties,Usage,Production

Uses

(R)-1-Benzylpyrrolidine-2-carboxylic acid is a proline derivative[1].

Synthesis

General procedure for the synthesis of N-benzyl-D-proline from benzyl chloride and D-proline: a suspension of D-proline (115 g, 1 mol), potassium hydroxide (168.3 g, 3 mol) and isopropanol (1 L) was stirred at 40°C until the suspension became clear. Subsequently, benzyl chloride (137.3 g, 1.1 mol) was slowly added and stirring was continued at 40°C for 6 hours. Upon completion of the reaction, the reaction mixture was cooled to 0-5°C and the pH was adjusted to 5-6 with concentrated hydrochloric acid (145 mL). the reaction mixture was diluted with chloroform (3 L) and stirred for 18 h. The reaction was purified by filtration. The resulting KCl was removed by filtration, the filtrate was concentrated and the crude product was recrystallized from acetone to give N-benzyl-D-proline in 79% yield (161.8 g). [39] The product was characterized as follows: 1H-NMR (CDCl3, ppm): δ 7.2-7.4 (m, 5H), 4.0-4.4 (dd, 2H), 3.8 (dd, 1H), 3.6-3.7 (m, 1H), 2.8 (dd, 1H), 1.8-2.4 (m, 4H). [40] Specific optical rotation [α]D25 = +28.4 (c = 1, EtOH). [41] Melting point 174-175°C.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368