N-trans-BOC-(3S)-Fluoropyrrolidine Chemical Properties

Boiling point:

74-80℃/2mm

Density 

1.069 g/mL at 25 °C

Flash point:

103°(217°F)

refractive index 

1.4410

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Liquid

pka

-3.60±0.40(Predicted)

color 

Colorless to pale yellow

Sensitive 

Moisture Sensitive

Safety Information

Hazard Codes 

T,N

Risk Statements 

25-36-50

Safety Statements 

26-45-61

RIDADR 

UN 2810 6.1 / PGIII

WGK Germany 

3

HazardClass 

6.1

HS Code 

2933998090

N-trans-BOC-(3S)-Fluoropyrrolidine Usage And Synthesis

Synthesis

1. Fluorination: To a solution of tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate (2.62 g) in dichloromethane (50 mL) was slowly added diethylaminosulfur trifluoride (2.22 mL) at -78°C. The mixture was gradually brought to room temperature and stirred for 75 minutes. The reaction mixture was gradually brought to room temperature and stirred for 75 minutes. 2. Post-treatment: The reaction mixture was poured into ice water and the organic layer was separated. The organic layer was dried with anhydrous magnesium sulfate and filtered to remove the desiccant. 3. Purification: The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate gradient) to afford tert-butyl (3S)-3-fluoropyrrolidine-1-carboxylate (676 mg, 26% yield) as an oily product. 4. 4. Product characterization: 1H-NMR (400 MHz, CDCl3) δ: 1.45 (9H, s), 2.17-2.26 (1H, m), 3.52-3.68 (5H, m), 5.20 (1H, dt, J = 52.7, 3.4 Hz).

References

[1] Patent: EP1785418, 2007, A1. Location in patent: Page/Page column 44
[2] Patent: WO2006/19833, 2006, A1. Location in patent: Page/Page column 62-63
[3] Patent: WO2006/40625, 2006, A1. Location in patent: Page/Page column 47-48
[4] Patent: WO2004/69256, 2004, A1. Location in patent: Page/Page column 48

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