| Identification | More | [Name]
(S)-1-Boc-2-cyanopyrrolidine | [CAS]
228244-04-0 | [Synonyms]
1-BOC-2-CYANO-PYRROLIDINE
1-N-BOC-2-CYANO-PYRROLIDINE
1-n-boc-2-pyrrolidinonitrile
2-CYANO-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
2-CYANOPYRROLIDINE, N-BOC PROTECTED
TERT-BUTYL 2-CYANOPYRROLIDINE-1-CARBOXYLATE
(s)-N-boc-2-cyano-piperidine
(S)-1-(tert-Butoxycarbonyl)-2-Pyrrolidinecarbonitrile
(S)-1-Boc-2-cyanopyrrolidine
(S)-1-BOC-2-Pyrrolidinecarbonitrile
(S)-1-Boc-2-cyanopiperidine | [Molecular Formula]
C10H16N2O2 | [MDL Number]
MFCD01861225 | [Molecular Weight]
196.25 | [MOL File]
228244-04-0.mol |
| Chemical Properties | Back Directory | [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) | [Fp ]
>110°C | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
powder to lump | [pka]
-4.97±0.40(Predicted) | [color ]
White to Orange to Green | [Optical Rotation]
[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 Data | Back Directory | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3439 | [WGK Germany ]
3 | [HS Code ]
29339900 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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 |
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| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|