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| | N-Boc-Piperidine-4-carboxylic acid methyl ester Basic information |
| | N-Boc-Piperidine-4-carboxylic acid methyl ester Chemical Properties |
| Melting point | 33.0 to 37.0 °C | | Boiling point | 307.4±35.0 °C(Predicted) | | density | 1.094±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Methanol | | form | powder to lump | | pka | -2.29±0.40(Predicted) | | color | White to Light yellow | | InChI | InChI=1S/C12H21NO4/c1-12(2,3)17-11(15)13-7-5-9(6-8-13)10(14)16-4/h9H,5-8H2,1-4H3 | | InChIKey | PTZNCCIULVXFIJ-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC(C(OC)=O)CC1 | | CAS DataBase Reference | 124443-68-1(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | HazardClass | IRRITANT | | HS Code | 29333990 |
| | N-Boc-Piperidine-4-carboxylic acid methyl ester Usage And Synthesis |
| Chemical Properties | White solid | | Uses | Methyl (1-BOC-piperidin-4-yl)carboxylate can be used as orexin type-2 receptor agonist. | | Synthesis | General procedure for the synthesis of methyl 1-tert-butoxycarbonyl-4-piperidinecarboxylate from methanol and 1-Boc-4-piperidinecarboxylic acid: a hexane solution of trimethylmethylsilyl diazomethane (2.00 M, 52.9 mL, 106 mmol) was added slowly and dropwise at 0 °C to a 1-tert-butoxycarbonyl-piperidine-4-carboxylic acid (12.14 g, 52.95 mmol) acetonitrile ( 100 mL) suspension. Methanol (10 mL) was then added. The reaction mixture was allowed to stand at 0 °C for 30 min and then stirred at room temperature for 3 h. The reaction was carried out under reduced pressure. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography [hexane/ethyl acetate (4.5:1, v/v)] to afford 1-tert-butyl 4-methylpiperidine-1,4-dicarboxylate as a colorless oil (11.5 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, d6-DMSO): δ 4.02 (dt, 2H, J = 3.5, 13.7 Hz), 3.69 (s, 3H), 2.82 (ddd, 2H, J = 3, 11.5, 14.5 Hz), 2.45 (tt, 1H, J = 3.9, 11.5 Hz), 1.90-1.84 ( m, 2H), 1.67-1.57 (m, 2H), 1.45 (s, 9H). Mass spectral analysis (ES) showed m/z 265.8 (MNa+); calculated value: 243.1 (M). | | References | [1] Patent: WO2006/86609, 2006, A2. Location in patent: Page/Page column 160
[2] Tetrahedron Letters, 2004, vol. 45, # 12, p. 2663 - 2665
[3] Tetrahedron Letters, 2011, vol. 52, # 8, p. 849 - 852 |
| | N-Boc-Piperidine-4-carboxylic acid methyl ester Preparation Products And Raw materials |
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