1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine Chemical Properties

Melting point:

88-91°C

Boiling point:

316.7±42.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-7.30±0.60(Predicted)

Appearance

White to off-white Solid

Safety Information

Risk Statements 

43

Safety Statements 

36/37

RIDADR 

UN3439

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933998090

1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine Usage And Synthesis

Synthesis

Step 2: Synthesis of (2S,4S)-1-Boc-2-cyano-4-fluoropyrrolidine To a stirred and cooled to 0 °C solution of (2S,4S)-N-Boc-4-fluoropyrrolidine-2-carboxamide (10 g, 43.10 mmol) in anhydrous THF (50 ml) was sequentially added triethylamine (13.93 g, 138 mmol) and trifluoroacetic anhydride (14.5 g, 69.05 mmol). The reaction mixture was continued to be stirred at 0°C for 1 hour. After completion of the reaction, the reaction was quenched with 100 ml of water and extracted with chloroform (2 x 100 ml). The organic phases were combined, washed sequentially with water (2 x 100 ml) and brine (50 ml) and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give 9.0 g of off-white solid product in 97.6% yield. IR (KBr, cm-1): 2979, 2243, 1387, 1240, 1168, 1123, 1072, 960. 1H NMR (CDCl3, 300MHz) δ: 1.49-1.53(d, rotary isomer, 9H), 2.25-2.47(m, 1H), 2.64(t, J=14.7Hz, 1H), 3.52(dd, J=9.6,3.6Hz, 0.5H, rotary isomer), 3.64(dd, J=9.3,3.3Hz , 0.5H, rotary isomer), 3.73-3.94 (m, 1H), 4.64 (dd, J=8.7 Hz, 0.6H, rotary isomer), 4.76 (dd, J=8.7 Hz, 0.4H, rotary isomer), 5.31 (brd, J=51.3 Hz, 1H).

References

[1] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 8, p. 1110 - 1117
[2] Patent: WO2005/75426, 2005, A1. Location in patent: Page/Page column 35-36
[3] Patent: WO2006/90244, 2006, A1. Location in patent: Page/Page column 29
[4] Patent: WO2006/40625, 2006, A1. Location in patent: Page/Page column 44
[5] Patent: WO2007/99385, 2007, A1. Location in patent: Page/Page column 26

1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine(426844-76-0)Related Product Information

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