(S)-1-BOC-2-METHYLPYRROLIDINE Chemical Properties

Boiling point:

234.0±9.0 °C(Predicted)

Density 

0.962 g/mL at 25 °C

refractive index 

n20/D 1.444

Flash point:

82 °C

storage temp. 

2-8°C

pka

-1.21±0.40(Predicted)

Appearance

Colorless to light yellow Liquid

optical activity

Consistent with structure

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-37/38-41-50

Safety Statements 

26-39-45-61

RIDADR 

UN 2810 6.1/PG 3

HazardClass 

8, 6.1

(S)-1-BOC-2-METHYLPYRROLIDINE Usage And Synthesis

Synthesis

Tert-butyl 2R-methanesulfonyloxymethylpyrrolidine-1-carboxylate (1.6 g, 5.73 mmol) was used as a raw material, and lithium triethylborohydride (1 M solution in THF, 17 mL, 17 mmol) was slowly added to its solution in 10 mL of tetrahydrofuran at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and water and washed sequentially with 0.1 N HCl and saturated saline. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated to give tert-butyl (S)-2-methylpyrrolidine-1-carboxylate as a colorless transparent oil (0.930 g, 88% yield). Its NMR hydrogen spectrum (400 MHz, CDCl3) data were as follows: δ 3.83 (m, 1H), 3.38 (m, 2H), 1.92 (m, 3H), 1.58 (m, 1H), 1.48 (s, 9H), 1.2 (d, J = 8 Hz, 3H).

References

[1] Patent: WO2006/19833, 2006, A1. Location in patent: Page/Page column 61
[2] Tetrahedron Letters, 1995, vol. 36, # 8, p. 1223 - 1226

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