1-Boc-3-Methylaminopyrrolidine Chemical Properties

Boiling point:

269 °C

Density 

1.03

Flash point:

117 °C

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

10.02±0.20(Predicted)

form 

solid

Appearance

Colorless to light yellow Liquid

optical activity

-1.16°(C=0.50g/100mL, CHCL3, 20°C, 589nm)

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-50

Safety Statements 

45-61

RIDADR 

UN2811

HazardClass 

8

HS Code 

29339900

1-Boc-3-Methylaminopyrrolidine Usage And Synthesis

Synthesis

GENERAL STEPS: To a solution of 1-(tert-butoxycarbonyl)pyrrolidin-3-one (74 g, 0.4 mol) in methanol (450 mL) was slowly added a methanolic solution of methylamine (137.8 g, 1.2 mol) at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, sodium borohydride (15.2 g, 0.4 mol) was added in batches and stirring was continued for 1 hour at room temperature. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was extracted by partitioning between dichloromethane (3 x 500 mL) and water (300 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 1-(tert-butoxycarbonyl)-3-methylaminopyrrolidine (74 g, 92.5% yield), which could be used in the next reaction without further purification. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.54 (m, 4H), 3.29 (m, 2H), 2.45 (s, 3H), 2.20 (m, 1H), 1.38 (s, 9H).

References

[1] Patent: WO2009/76387, 2009, A1. Location in patent: Page/Page column 42
[2] Patent: US2015/252021, 2015, A1. Location in patent: Paragraph 0307; 0308
[3] Patent: WO2012/127506, 2012, A1. Location in patent: Page/Page column 108-109
[4] ChemCatChem, 2018, vol. 10, # 3, p. 510 - 514
[5] Patent: WO2007/122410, 2007, A1. Location in patent: Page/Page column 101; 106

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