(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester CAS 361440
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester Basic information
| Product Name: | (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester |
| Synonyms: | (1S,3S,5S)-3-Aminocarbonyl-2-Azabicyclo[3.1.0]Hexane-2-Carboxylicacid,1,1-Dimethylethyl Ester;Saxagliptin int;(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester;(1S,3S,5S)-3-(AMinocarbonyl)-2-azabicylo[3.1.0]hexane-2-carboxylic acid tert-butyl ester;(1S,3S,5S)-3-(AMinocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid;(1S,3S,5S)-tert-butyl 3-carbaMoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate;N-Boc-L-cis-4,5-MethanoprolineaMide;(1S,3S,5S)-3-(AMinocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl este |
| CAS: | 361440-67-7 |
| MF: | C11H18N2O3 |
| MW: | 226.27 |
| EINECS: | 1308068-626-2 |
| Product Categories: | |
| Mol File: | 361440-67-7.mol |
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester Chemical Properties
| Boiling point | 388.9±21.0 °C(Predicted) |
| density | 1.228 |
| storage temp. | 2-8°C |
| pka | 16.00±0.20(Predicted) |
| Appearance | White to off-white Solid |
| InChI | InChI=1S/C11H18N2O3/c1-11(2,3)16-10(15)13-7-4-6(7)5-8(13)9(12)14/h6-8H,4-5H2,1-3H3,(H2,12,14)/t6-,7-,8-/m0/s1 |
| InChIKey | VLAGXRRGXCNITB-FXQIFTODSA-N |
| SMILES | [C@@]12([H])[C@@]([H])(C1)C[C@@H](C(N)=O)N2C(OC(C)(C)C)=O |
Safety Information
| Uses | N-Boc-L-cis-4,5-Methanoprolineamide is an intermediate used to prepare methanoprolinenitrile-contg. dipeptide mimetics as DPP-IV inhibitors and as antidiabetic agents. |
| Synthesis | 197142-36-2 361440-67-7 At -15°C, (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1.2 g) was dissolved in THF (20 ml) and 4-methylmorpholine (710 μl) was added. Subsequently, isobutyl chloroformate (780 μl) was added slowly over a period of 5 min and stirring was continued at this temperature for 30 min. The reaction system was cooled to -30°C and aqueous ammonia solution (25 ml, 0.5 M) dissolved in dioxane was slowly added. The reaction mixture was stirred at -30 °C for 30 min and then gradually warmed to room temperature and continued stirring overnight. After completion of the reaction, the pH was adjusted to 4.5 with 10% aqueous citric acid solution and extracted with ether (3 x 50 ml). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Finally, purification by silica gel column chromatography (eluent: cyclohexane/ethyl acetate, 1:10) afforded the target product (1S,3S,5S)-tert-butyl (1.0 g, 84% yield, MNa+ = 248) of (1S,3S,5S)-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate. |
| References | [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2587 - 2598 [2] Patent: WO2006/116157, 2006, A2. Location in patent: Page/Page column 114-116 [3] Patent: EP2272825, 2015, B1. Location in patent: Paragraph 0182; 0183 [4] Patent: CN106928124, 2017, A. Location in patent: Paragraph 0037; 0095-0100 |
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester Preparation Products And Raw materials
| Raw materials | 1H-Pyrrole-1-carboxylic acid, 2-(aMinocarbonyl)-2,3-dihydro-, 1,1-diMethylethyl ester, (2S)--->(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID-->Tetramethylammonium trifluoromethanesulfonate-->Diiodomethane-->Dibromomethane-->Ammonia-->Tetrahydrofuran-->1,4-Dioxane-->Isobutyl chloroformate-->4-Methylmorpholine |
| Preparation Products | (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate |
