|
|
| | (S)-3-Amino-1-N-Boc-piperidine Basic information |
| | (S)-3-Amino-1-N-Boc-piperidine Chemical Properties |
| alpha | -28.5 º (c=1, DMF) | | Boiling point | 277.3±33.0 °C(Predicted) | | density | 1.02 | | refractive index | 1.4690-1.4730 | | Fp | 122℃ | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | Soluble in dimethylsulfoxide. | | pka | 10.35±0.20(Predicted) | | form | Gum or Semi-Solid | | color | Colorless to yellow | | Optical Rotation | [α]/D +32.0±3°, c = 1 in DMF | | Sensitive | Air Sensitive | | InChI | InChI=1S/C10H20N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(11)7-12/h8H,4-7,11H2,1-3H3/t8-/m0/s1 | | InChIKey | AKQXKEBCONUWCL-QMMMGPOBSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC[C@H](N)C1 | | CAS DataBase Reference | 625471-18-3(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | RIDADR | 2735 | | WGK Germany | 3 | | F | 10-34 | | HazardClass | 8 | | HS Code | 29333990 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (S)-3-Amino-1-N-Boc-piperidine Usage And Synthesis |
| Chemical Properties | Light yellow liquid | | Uses | (S)-(+)-3-Amino-1-Boc-piperidine is used to prepare selective noncovalent inhibitors of the bacterial cysteine protease IdeS. The product obtained by the reductive elimination reaction with ethylglyoxalte is used as a reference compound, which is used to determine the absolute configuration of the two enantiomers. | | Synthesis | General procedure for the synthesis of (S)-1-Boc-3-aminopiperidine from the compound (CAS:1271240-70-0): the azido derivative 42a (6.77 g, 29.9 mmol) was mixed with Pd/C catalyst (150 mg) in ethanol (200 mL) and subjected to a hydrogenation reaction at atmospheric pressure overnight. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration followed by evaporation of the solvent. The product 43a was obtained as a colorless liquid in 90% yield (5.39 g, 26.9 mmol) without further purification. The 1H NMR, 13C NMR and IR spectral data of the product were in agreement with those reported in the literature30 . High-resolution mass spectrometry (HRMS, ESI) analysis showed a calculated and measured value of 201.1598 for C10H21O2N2 ([M + H]+); the specific spin [α]D20 was +26.0 (c 0.308, EtOH). | | References | [1] Tetrahedron, 2011, vol. 67, # 7, p. 1485 - 1500
[2] Patent: WO2005/305, 2005, A1. Location in patent: Page 60
[3] Patent: WO2005/20976, 2005, A2. Location in patent: Page/Page column 239
[4] Patent: WO2005/60949, 2005, A2. Location in patent: Page/Page column 238 |
| | (S)-3-Amino-1-N-Boc-piperidine Preparation Products And Raw materials |
|