(R)-2-Methylpyrrolidine hydrochloride Chemical Properties

Melting point:

73.0 to 77.0 °C

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystaline

color 

White to Almost white

optical activity

Consistent with structure

InChI

InChI=1/C5H11N.ClH/c1-5-3-2-4-6-5;/h5-6H,2-4H2,1H3;1H/t5-;/s3

InChIKey

JNEIFWYJFOEKIM-USHJBNIQNA-N

SMILES

C[C@H]1NCCC1.Cl |&1:1,r|

CAS DataBase Reference

135324-85-5(CAS DataBase Reference)

Safety Information

HS Code 

2933998090

(R)-2-Methylpyrrolidine hydrochloride Usage And Synthesis

Synthesis

Step B: (i) Synthesis of (R)-2-methylpyrrolidine hydrochloride; (i) (R)-tert-butyl 2-methylpyrrolidine-1-carboxylate (22.7 g, 123 mmol) was dissolved in 4 M hydrogen chloride in dioxane solution (100 mL) and the reaction was stirred for 30 min at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio 2:1 ethyl acetate/hexane) to confirm complete consumption of the raw material. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was dissolved in a solvent mixture of acetonitrile and toluene and the solvent was again removed by distillation under reduced pressure. The resulting white solid was dried overnight under reduced pressure to give (R)-2-methylpyrrolidine hydrochloride (14.6 g) in 98% yield. The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shifts δ 1.55 (d, J = 6.57 Hz, 3H), 1.66-1.77 (m, 1H), 1.95-2.04 (m, 1H), 2.05-2.23 (m, 2H), 3.25-3.36 (m, 1H), 3.37-3.48 (m, 1H), and 3.62-3.74 (m, 1H), 9.38 (s, 1H), 9.86 (s, 1H).

References

[1] Patent: WO2008/5338, 2008, A1. Location in patent: Page/Page column 80
[2] Tetrahedron, 2006, vol. 62, # 18, p. 4584 - 4589
[3] Patent: US2004/260100, 2004, A1. Location in patent: Page 8
[4] Patent: WO2006/19833, 2006, A1. Location in patent: Page/Page column 44
[5] Organic and Biomolecular Chemistry, 2010, vol. 8, # 20, p. 4533 - 4535

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