| Identification | Back Directory | [Name]
tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate | [CAS]
900503-08-4 | [Synonyms]
-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate
8-Boc-8-aza-bicyclo3.2.1oct-2-ene-3-boronic acid picol ester
8-Boc-8-azabicyclo[3.2.1]oct-2-ene-3-boronic acid pinacol ester
8-Boc-8-azabicyclo[3.2.1]oct-3-ene-3-boronic acid pinacol ester
N-BOC-8-AZABICYCLO[3.2.1]OCT-2-ENE-2-BORONIC ACID, PINACOL ESTER
8-(tert-Butoxy)carbonyl-8-azabicyclo[3.2.1]oct-2-ene-3-boronic acid pinacol ester
8-Boc-3-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene
(8-(TERT-BUTOXYCARBONYL)-8-AZABICYCLO[3.2.1]OCT-2-EN-3-YL)BORONIC ACID PINACOL ESTER
tert-butyl3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
tert-butyl 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylat
tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate
tert-butyl 3-(hydroxy((3-hydroxy-2,3-dimethylbutan-2-yl)oxy)boryl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylic acid tert-butyl ester
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid 1,1-dimethylethyl ester
8-Azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-diMethylethyl ester | [Molecular Formula]
C18H30BNO4 | [MDL Number]
MFCD13184779 | [MOL File]
900503-08-4.mol | [Molecular Weight]
335.25 |
| Chemical Properties | Back Directory | [Boiling point ]
378.2±52.0 °C(Predicted) | [density ]
1.08 | [storage temp. ]
Sealed in dry,2-8°C | [pka]
-1.34±0.40(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C18H30BNO4/c1-16(2,3)22-15(21)20-13-8-9-14(20)11-12(10-13)19-23-17(4,5)18(6,7)24-19/h10,13-14H,8-9,11H2,1-7H3 | [InChIKey]
JNHGCLCLMOCPCQ-UHFFFAOYSA-N | [SMILES]
C12N(C(OC(C)(C)C)=O)C(CC1)CC(B1OC(C)(C)C(C)(C)O1)=C2 |
| Hazard Information | Back Directory | [Synthesis]
8-Boc-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene (10.1 g, 28.4 mmol) and pinacol ester of bis(boronic acid) (8.7 g, 34.1 mmol) were added under argon protection with KOAc (8.4 g, 85.3 mmol), PdCl2(dppf)2-CH2Cl2 ( 1.4 g, 1.7 mmol) and dppf (1 g, 1.8 mmol) in dioxane (170 ml). The reaction mixture was stirred at 80°C for 16 hours. After completion of the reaction, it was cooled to room temperature and the solvent was removed by rotary evaporation. The crude product was redissolved in EtOAc (500 ml), washed sequentially with water (125 ml) and brine (125 ml) and dried over anhydrous Na2SO4. The solvent was removed by concentration under reduced pressure and the residue was purified by silica gel column chromatography eluting with EtOAc/hexane (0-40%) gradient to afford the target product 8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene-3-boronic acid pinacol ester (8.6 g, 90% yield). | [References]
[1] Patent: WO2012/27234, 2012, A1. Location in patent: Page/Page column 41; 42
[2] Patent: WO2014/9296, 2014, A1. Location in patent: Page/Page column 93
[3] Patent: US2015/191482, 2015, A1. Location in patent: Paragraph 0476
[4] Patent: US2017/112833, 2017, A1. Location in patent: Paragraph 0520-0521
[5] Canadian Journal of Chemistry, 2006, vol. 84, # 4, p. 555 - 560 |
|
|