1-Boc-3-piperidinecarboxylic acid CAS 84358-12-3
1-Boc-3-piperidinecarboxylic acid Basic information
| Product Name: | 1-Boc-3-piperidinecarboxylic acid |
| Synonyms: | 1-N-Boc-3-piperidinecarboxylicacid;(R,S)-N-T-BUTYLOXYCARBONYL-NIPECOTIC ACID, (R,S)-N-T-BUTYLOXYCARBONYL-PIPERIDINE-3-CARBOXYLIC ACID;N-BOC-DL-NIPECOTIC ACID;(+/-)-N-BOC-NIPECOTIC ACID;N-BOC-NIPECOTIC ACID;(+/-)-N-BOC-PIPERIDINE-3-CARBOXYLIC ACID;N-BOC-PIPERIDINE-3-CARBOXYLIC ACID;N-ALPHA-T-BOC-3-CARBOXYPIPERIDINE |
| CAS: | 84358-12-3 |
| MF: | C11H19NO4 |
| MW: | 229.27 |
| EINECS: | |
| Product Categories: | Piperidines;Carboxylic Acids;Pyrans, Piperidines & Piperazines;Carboxylic Acids;Pyrans, Piperidines &Piperazines;Piperidine;API intermediates;Others;Peptide Synthesis;Unnatural Amino Acid Derivatives |
| Mol File: | 84358-12-3.mol |
1-Boc-3-piperidinecarboxylic acid Chemical Properties
| Melting point | 159-162 °C(lit.) |
| Boiling point | 353.2±35.0 °C(Predicted) |
| density | 1.164±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| pka | 4.49±0.20(Predicted) |
| form | Crystalline Powder |
| color | White |
| BRN | 5539297 |
| Major Application | peptide synthesis |
| InChI | InChI=1S/C11H19NO4/c1-11(2,3)16-10(15)12-6-4-5-8(7-12)9(13)14/h8H,4-7H2,1-3H3,(H,13,14) |
| InChIKey | NXILIHONWRXHFA-UHFFFAOYSA-N |
| SMILES | N1(C(OC(C)(C)C)=O)CCCC(C(O)=O)C1 |
| CAS DataBase Reference | 84358-12-3(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | White crystalline powder |
| Uses | peptide synthesis |
| reaction suitability | reaction type: solution phase peptide synthesis |
| Synthesis | 24424-99-5 498-95-3 71381-75-4 The general procedure for the synthesis of 1-BOC-piperidine-3-carboxylic acid from di-tert-butyl dicarbonate and 3-piperidinecarboxylic acid is as follows:1. Dissolve piperidine-3-carboxylic acid (50.0 g, 387.5 mmol) in tert-butyl alcohol (464.0 mL) at 0 °C, slowly add 1N NaOH solution (464.0 mL), and stir for 10 min. 2. Add di-tert-butyl dicarbonate (Boc-anhydride, 143.6 g, 659.0 mmol) to the above solution. 3. Stir the reaction mixture for 12 hours at room temperature. 4. Di-tert-butyl carbonate (Boc-anhydride, 143.6 g, 659.0 mmol) was added to the above solution. 3. The reaction mixture was stirred at room temperature for 12 h. 4. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure, and then neutralized to pH neutral with 1N HCl solution. 5. The precipitated white solid was collected by filtration, and dried to give 1-BOC-piperidine-3-carboxylic acid (1 , 86.0 g, yield 97%). The product was characterized by 1H NMR (400 MHz, DMSO-d6), δ 1.38 (s, 9H), 1.47 (m, 1H), 1.59 (dt, J = 3.8 Hz, 1H), 1.87 (m, 1H), 2.28 (m, 1H), 2.77-2.84 (dt, J = 2.5,3.0 Hz, 1H), 3.0 (brs. 1H), 3.67 (d, J = 11.0 Hz, 1H), 3.87 (brs, 1H), 12.2 (s, 1H). |
| References | [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2118 - 2122 [2] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 00604 [3] Journal of Medicinal Chemistry, 2004, vol. 47, # 7, p. 1719 - 1728 [4] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 966 - 973 [5] European Journal of Organic Chemistry, 2005, # 4, p. 673 - 682 |
1-Boc-3-piperidinecarboxylic acid Preparation Products And Raw materials
| Raw materials | Di-tert-butyl dicarbonate-->Nipecotic acid-->tert-Butanol-->Sodium hydroxide |
