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

Boiling point:

361.4±42.0 °C(Predicted)

Density 

1.19±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

13.90±0.40(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C10H16N2O3/c1-10(2,3)15-9(14)12-6-8(13)4-7(12)5-11/h7-8,13H,4,6H2,1-3H3/t7-,8+/m0/s1

InChIKey

UNVNZVOSYRUJTH-JGVFFNPUSA-N

SMILES

N1(C(OC(C)(C)C)=O)C[C@H](O)C[C@H]1C#N

Safety Information

HS Code 

2933998090

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

Synthesis

General procedure for the synthesis of (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine from (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine: 7.82 g (34 mmol) of (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine was dissolved in 80 mL of pyridine, followed by a slow addition of 12 mL (84 mmol) trifluoroacetic anhydride. The reaction mixture was cooled to -20 °C and the reaction was stirred at this temperature. Upon completion of the reaction, the mixture was warmed to room temperature and stirring was continued for 24 hours. The excess trifluoroacetic anhydride was quenched by adding an appropriate amount of water. To the reaction mixture was added 200 mL of ethyl acetate, and the organic layer was washed sequentially with 10% aqueous hydrochloric acid (adjusting the pH to 3-5), 50 mL of 2 N sodium hydroxide solution, and 50 mL of saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oily product. Yield: 5.35 g (74% yield).

References

[1] Patent: WO2003/106456, 2003, A2. Location in patent: Page 28
[2] Patent: EP2246347, 2010, A1. Location in patent: Page/Page column 39