METHYL N-BENZYL-3-PYRROLIDINECARBOXYLATE Chemical Properties

Boiling point:

98℃/0.2mm

Density 

1.08

refractive index 

1.5211

storage temp. 

2-8°C

form 

clear liquid

pka

8.34±0.40(Predicted)

color 

Colorless to Light orange to Yellow

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

InChI

InChI=1S/C13H17NO2/c1-16-13(15)12-7-8-14(10-12)9-11-5-3-2-4-6-11/h2-6,12H,7-10H2,1H3

InChIKey

GDWFCUOFVSNTTG-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(C(OC)=O)C1

CAS DataBase Reference

17012-21-4

Safety Information

HS Code 

2933998090

METHYL N-BENZYL-3-PYRROLIDINECARBOXYLATE Usage And Synthesis

Uses

It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 3637, 1968 DOI: 10.1021/jo01273a063

Synthesis

A trifluoroacetic acid solution of 44.0 g (0.4 mol) at a mass concentration of 10% was prepared by adding 1530.0 g (6.5 mol) of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, 31.80 g (3.7 mol) of methyl acrylate, and 38 mL of dichloromethane to a 250 mL multi-neck reaction flask. The trifluoroacetic acid solution was added slowly dropwise at 0 °C, and after completion of the dropwise addition, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure and the residue was washed sequentially with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 1420.0 g of 1-benzylpyrrolidine-3-carboxylic acid methyl ester crude product in 100% yield.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 19, p. 4861 - 4866
[2] Organic Process Research and Development, 2009, vol. 13, # 2, p. 292 - 296
[3] Synthesis, 2006, # 16, p. 2646 - 2648
[4] Synlett, 2015, vol. 26, # 13, p. 1815 - 1818
[5] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 7, p. 2762 - 2766

METHYL N-BENZYL-3-PYRROLIDINECARBOXYLATE(17012-21-4)Related Product Information

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