(R)-2-Methyl-pyrrolidine Chemical Properties

Boiling point:

94 °C(Press: 728 Torr)

Density 

0.842

refractive index 

1.4353

Flash point:

45 ºF

storage temp. 

2-8°C

pka

10.93±0.10(Predicted)

form 

oil

color 

Colourless to pale yellow

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C5H11N/c1-5-3-2-4-6-5/h5-6H,2-4H2,1H3/t5-/m1/s1

InChIKey

RGHPCLZJAFCTIK-RXMQYKEDSA-N

SMILES

N1CCC[C@H]1C

CAS DataBase Reference

41720-98-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,F

Risk Statements 

11-22-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2924

WGK Germany 

3

Hazard Note 

Corrosive/Highly Flammable

HazardClass 

3

PackingGroup 

Ⅱ

HS Code 

29339900

(R)-2-Methyl-pyrrolidine Usage And Synthesis

Uses

It is used as a building block used in a multikilogram synthesis of a chiral naphthalenoid histamine receptor antagonist.

Definition

ChEBI: (R)-2-methylpyrrolidine is a 2-methylpyrrolidine that has (R)-configuration. It is a conjugate base of a (R)-2-methylpyrrolidinium.

Application

(R)-2-Methyl-pyrrolidine, an optically active amine that can be used as a key building block to synthesize:
4,5-fused pyridazinone derivatives are applicable as potent histamine H3 receptor antagonists.
Naphthalenoid histamine H3 receptor antagonist.
Pyrrolo[2,3-d]pyrimidine derivatives as potent inhibitors of leucine-rich repeat kinase 2.

Synthesis

The general procedure for the synthesis of 2-methylpyrrolidine from 2-methylpyrroline was as follows: the whole-cell biotransformation reaction was carried out in sodium phosphate buffer (100 mM, pH 7.0) at 30 °C and 1000 rpm. Freshly harvested resting cells of E. coli BL21(DE3) expressing IRED with a final OD600nm adjusted to 90 were used.The reaction mixture contained 2.5 or 5 mM of imine substrate and 50 mM of glucose.

References

Synthesis and structure-activity relationships of 4,5-fused pyridazinones as histamine H3 receptor antagonists. DOI:10.1016/j.bmcl.2011.08.045
Efficient and Practical Synthesis of (R)-2-Methylpyrrolidine DOI:10.1021/jo060319n

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