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| | tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Basic information | | Uses |
| Product Name: | tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate | | Synonyms: | 3,8-Diazabicyclo[3.2.1]octane-8-carboxylic acid, 3-(phenylMethyl)-, 1,1-diMethylethyl ester;3-Benzyl-8-Boc-3,8-diaza-bicyclo[3.2.1]octane;8-Boc-3-benzyl-3,8-diazabicyclo[3.2.1]octane;3-benzyl-8-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]-octane;3-benzyl-3,8-diazabiscyclo[3.2.1]octylalkane-8-carboxylic acidtertbutyl ester;tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate | | CAS: | 149771-43-7 | | MF: | C18H26N2O2 | | MW: | 302.41 | | EINECS: | | | Product Categories: | | | Mol File: | 149771-43-7.mol | ![tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Structure](CAS/GIF/149771-43-7.gif) |
| | tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical Properties |
| Boiling point | 393.4±35.0 °C(Predicted) | | density | 1.117±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | 8.57±0.20(Predicted) | | Appearance | White to off-white Solid |
| | tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Usage And Synthesis |
| Uses | 3-Benzyl-8-(tert-butoxycarbonyl)-3,8-diazabicyclo[3.2.1]-octane is a hydrocarbon derivative that can be used as a pharmaceutical intermediate. | | Synthesis | 3-Benzyl-3,8-diazabicyclo[3.2.1]octane (13.5 g, 66.7 mmol) was used as starting material and mixed with triethylamine (6.75 g, 66.7 mmol) and di-tert-butyl dicarbonate (14.56 g, 66.7 mmol) in dichloromethane (100 ml). The reaction mixture was stirred under cooling in an ice bath for 3 hours. After completion of the reaction, the crude product was washed with water (150 ml) and the aqueous phase was then extracted with dichloromethane (50 ml). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give tert-butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (13 g, 65% yield). The melting point of the product was 58-60°C. | | References | [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[2] Farmaco, 1993, vol. 48, # 3, p. 387 - 396
[3] Patent: EP1213289, 2002, A1. Location in patent: Page 12
[4] Patent: WO2006/106090, 2006, A1. Location in patent: Page/Page column 16
[5] Farmaco, 1998, vol. 53, # 8-9, p. 557 - 562 |
| | tert-Butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Preparation Products And Raw materials |
| Raw materials | D-Proline, 1-(phenylmethyl)-5-[[(phenylmethyl)amino]carbonyl]-, ethyl ester, (5S)--->3-Benzyl-3,8-diazabicyclooctane[3.2.1]-2,4-dione-->3,8-dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione-->Diethyl meso-2,5-dibromoadipate-->8-Boc-3,8-diaza-bicyclo[3.2.1]octane-->(1-Benzylpyrrolidine-2,5-diyl)diMethanol-->1-Boc-2,5-bis-hydroxymethyl-pyrrolidine-->tert-butyl 2,5-bis(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate-->diethyl 1-benzylpyrrolidine-2,5-dicarboxylate-->3-Benzyl-3,8-diazabicyclo[3.2.1]octane-->Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate-->Benzaldehyde-->Di-tert-butyl dicarbonate-->Sodium bicarbonate-->Benzyl bromide |
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