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| | 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER Basic information |
| Product Name: | 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER | | Synonyms: | 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, N-CBZ protected 97%;Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate;1-Benzyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 98%;N-Cbz-1,2,5,6-tetrahydropyridine-4-boronic acid;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl e;benzyl 4-(hydroxy((3-hydroxy-2,3-dimethylbutan-2-yl)oxy)boryl)-5,6-dihydropyridine-1(2H)-carboxylate;Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate;benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate | | CAS: | 286961-15-7 | | MF: | C19H26BNO4 | | MW: | 343.23 | | EINECS: | | | Product Categories: | | | Mol File: | 286961-15-7.mol | ![4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER Structure](CAS/GIF/286961-15-7.gif) |
| | 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER Chemical Properties |
| Melting point | 88-90℃ | | Boiling point | 418.2±55.0 °C(Predicted) | | density | 1.13 | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | form | Solid | | pka | -1.26±0.40(Predicted) | | color | Off-white | | InChI | InChI=1S/C19H26BNO4/c1-18(2)19(3,4)25-20(24-18)16-10-12-21(13-11-16)17(22)23-14-15-8-6-5-7-9-15/h5-10H,11-14H2,1-4H3 | | InChIKey | QDSFHRPYZPQWEJ-UHFFFAOYSA-N | | SMILES | C1N(C(OCC2=CC=CC=C2)=O)CC=C(B2OC(C)(C)C(C)(C)O2)C1 | | CAS DataBase Reference | 286961-15-7 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37 | | TSCA | No | | HS Code | 2933399990 |
| | 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER Usage And Synthesis |
| Uses | Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate is a reactant used in the synthesis of potent and orally bioavailable inhibitors of βII tryptase used in the treatment of allergic diseases. | | Synthesis | N-Benzyloxycarbonyl-3,6-dihydro-2H-pyridine-4-boronic acid pinacol ester was synthesized from bis(pinacolato) boronic acid and the compound (CAS: 286961-24-8) according to the method reported in Tetrahedron Lett. The steps were as follows: bis(pinacolato)ethylborane (338 mg, 1.33 mmol), potassium acetate (356 mg, 3.63 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PdCl2dppf; 30 mg, 0.04 mmol), and 1,1'-bis(diphenylphosphino)ferrocene ( 20 mg, 0.04 mmol), followed by addition of the product of Example 58A (440 mg, 1.21 mmol) in degassed 1,4-dioxane (7 mL). The reaction mixture was heated at 80 °C for 16 h, after which it was cooled to 23 °C, diluted with water and extracted with dichloromethane (3×). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by fast column chromatography on silica gel (eluent: 20% ethyl acetate/hexane) to afford the target product N-benzyloxycarbonyl-3,6-dihydro-2H-pyridine-4-boronic acid pinacol ester (323 mg, 78% yield). The product was confirmed by 1H NMR (300 MHz, CDCl3) and mass spectrometry (ESI): 1H NMR δ 1.25 (s, 12H), 2.24 (m, 2H), 3.52 (dd, 2H, J = 5.7, 5.7 Hz), 4.03 (dd, 2H, J = 6 Hz), 5.14 (s, 2H), 6.46 (br m, 1H), 7.32 (m, 5H); MS (ESI) m/e 344 (M + H)+. | | References | [1] Tetrahedron Letters, 2000, vol. 41, # 19, p. 3705 - 3708
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7450 - 7465
[3] Patent: US2003/229094, 2003, A1. Location in patent: Page 76
[4] Patent: US2003/232836, 2003, A1. Location in patent: Page 52
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 8, p. 2859 - 2872 |
| | 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER Preparation Products And Raw materials |
| Raw materials | Bis(pinacolato)diboron-->1,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-
dioxaborolan-2-yl)pyridine hydrochloride-->Benzyl chloroformate-->1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-4-[[(trifluoroMethyl)sulfonyl]oxy]-, phenylMethyl ester-->1,4-Dioxane-->Potassium Acetate | | Preparation Products | N-CBZ-1,2,3,6-tetrahydropyridin-4-ylboronic acid |
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