- N-T-BOC-PYRROLE
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- $7.00 / 1KG
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2019-09-03
- CAS:5176-27-2
- Min. Order: 1KG
- Purity: 99%
- Supply Ability: JD 832
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| | N-T-BOC-PYRROLE Basic information |
| | N-T-BOC-PYRROLE Chemical Properties |
| Boiling point | 91-92 °C20 mm Hg(lit.) | | density | 1 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.4685(lit.) | | Fp | 167 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | Acetonitrile, Dichloromethane, Ethyl Acetate, Methanol, Tetrahydrofuran | | pka | -6.10±0.70(Predicted) | | form | Solution | | color | Colorless to yellow | | InChI | InChI=1S/C9H13NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H,1-3H3 | | InChIKey | IZPYBIJFRFWRPR-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)C=CC=C1 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | HS Code | 2933998090 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | N-T-BOC-PYRROLE Usage And Synthesis |
| Chemical Properties | Colorless liquid | | Uses | Pyrrole-1-carboxylic Acid tert-Butyl Ester is an intermediate in the synthesis of pyrrole derived anti-cancer Agent. | | Uses | N-Boc-pyrrole was used in the synthesis of 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid by treating with n-BuLi and subsequent reaction with trimethyl borate.
It may be used as starting material in the synthesis of the following:
- tropane drivatives
- N-boc-2-(4-methoxyphenyl)pyrrole
- N-boc-pyrrol-2-ylboronic acid
| | Synthesis Reference(s) | The Journal of Organic Chemistry, 31, p. 764, 1966 DOI: 10.1021/jo01341a027 | | General Description | N-Boc-pyrrole is an N-protected pyrrole. It undergoes Diels–Alder reaction with enantiomerically pure allene-1,3-dicarboxylates to form endo-adducts with retention in configurations at two newly generated stereogenic centers. It also undergoes cyclopropanation with methyl phenyldiazoacetate to form both monocyclopropane and dicyclopropane. Its Ir-catalyzed C-H borylation followed by cross coupling with 3-chlorothiophene to form biheterocycle has been reported. | | Synthesis | General procedure for the synthesis of tert-butyl 1-pyrrolecarboxylate from pyrrole and di-tert-butyl dicarbonate: di-tert-butyl dicarbonate (Boc2O, 9.8 g, 44.7 mmol) and triethylamine (TEA, 6.3 mL, 44.7 mmol) were added sequentially to a solution of pyrrole (3.0 g, 29.8 mmol) in dichloromethane (DCM, 15 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, extraction was performed with dichloromethane (2 x 400 mL) and water (400 mL). The organic layers were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to afford tert-butyl 1-pyrrolecarboxylate (26) as a white solid (7.5 g). Yield: 94%; 1H NMR (300 MHz, CDCl3) δ (ppm): 7.26 (s, 2H), 7.24 (t, J=2.4 Hz, 1H), 6.22 (t, J=2.4 Hz, 1H), 1.60 (d, J=11.7 Hz, 9H); ESI-MS [M+H]+=169.0. | | References | [1] European Journal of Organic Chemistry, 2005, # 11, p. 2207 - 2212
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 52, p. 15739 - 15743
[3] Angew. Chem., 2015, vol. 127, # 52, p. 15965 - 15969,5
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1153 - 1164
[5] Medicinal Chemistry, 2018, vol. 14, # 5, p. 485 - 494 |
| | N-T-BOC-PYRROLE Preparation Products And Raw materials |
| Raw materials | 1H-Pyrrole-1-carboxylic acid, 2-(tributylstannyl)-, 1,1-dimethylethyl ester-->1H-Pyrrole-1-carboxylic acid, 2-(4-methoxyphenyl)-, 1,1-dimethylethyl ester-->N-Boc-pyrroline-->ISOPROPYLLITHIUM-->2-[(4-Methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hepta-2,5-diene-7-carboxylic acid tert-butyl ester-->TERT-BUTYL N-ALLYLCARBAMATE-->3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane-->Pyrrole-->Di-tert-butyl dicarbonate-->Crotonaldehyde (trans predominantly) | | Preparation Products | Isoxazole, 3-(2,4,6-trimethylphenyl)--->3-Phenylisoxazole |
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