(S)-1-Boc-2-cyanopyrrolidine Chemical Properties

Melting point:

33-36°C

alpha 

-105.5 º (c=1, chloroform)

Boiling point:

307.9±35.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

Flash point:

>110°C

storage temp. 

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

pka

-4.97±0.40(Predicted)

form 

powder to lump

color 

White to Orange to Green

optical activity

[α]20/D 105.5°, c = 1 in chloroform

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture & Light Sensitive

InChI

InChI=1S/C10H16N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(12)7-11/h8H,4-6H2,1-3H3/t8-/m0/s1

InChIKey

MDMSZBHMBCNYNO-QMMMGPOBSA-N

SMILES

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

CAS DataBase Reference

228244-04-0(CAS DataBase Reference)

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3439

WGK Germany 

3

HS Code 

29339900

(S)-1-Boc-2-cyanopyrrolidine Usage And Synthesis

Uses

(S)-(-)-1-Boc-2-pyrrolidinecarbonitrile is used in synthesis of prolyl oligopeptidase inhibitors and is a reagent that is used in the design of potent and selective inhibitors of DPP-4 that exhibits an attractive pharmacokinetic profile as antidiabetics.

Uses

Used in synthesis of prolyl oligopeptidase inhibitors.

Synthesis

GENERAL METHODS: N-Boc-L-prolinamide (5 g, 23.3 mmol) and cyanuric chloride (2.58 g, 14.0 mmol) were dissolved in DMF (10 mL), and the reaction was stirred at room temperature for 1 h (the reaction progress was monitored by TLC). After completion of the reaction, the reaction mixture was extracted with EtOAc, the organic phase was washed sequentially with water and saturated saline, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (1/1, v/v) as eluent to afford (S)-1-N-Boc-2-pyrrolidinecarbonitrile (3.48 g, 76% yield) as a white solid.1H NMR (300 MHz, CDCl3) δ 4.76 (s, 1H), 3.51 (s, 2H), 2.34-2.31 (m 1H), 2.17-2.10 (m, 2H), 1.90-1.87 (m, 1H), 1.49 (s, 9H).MS (ESI) m/z 197 [M + H]+.

References

[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 35, p. 8544 - 8551
[2] Canadian Journal of Chemistry, 2007, vol. 85, # 2, p. 85 - 95
[3] Synthetic Communications, 2009, vol. 39, # 3, p. 395 - 406
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 23, p. 7418 - 7429
[5] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 111 - 122

(S)-1-Boc-2-cyanopyrrolidine(228244-04-0)Related Product Information

• tert-Butanol
• N-Vinyl-2-pyrrolidone
• Polyvinylpyrrolidone
• Povidone iodine
• Crospovidone
• N-Methyl-2-pyrrolidone
• (S)-1-Boc-3-(hyroxymethyl)piperidine
• BOC-L-Prolinol
• tert-butyl (S)-2-(4-phenylthiazol-2-yl)pyrrolidine-1-carboxylate
• 1-Boc-3-cyanopyrrolidine,N-1-BOC-3-CYANOPYRROLIDINE
• (R)-1-Boc-2-cyanopyrrolidine
• (S)-1-BOC-3-Cyanopyrrolidine
• (S)-(-)-BOC-2-CYANOPYRROLIDINE
• (R)-1-Boc-3-cyanopyrrolidine
• METHYL-2-PYRROLIDONE
• (S)-1-Boc-2-cyanopyrrolidine