3-Aminocarbonyl-1-Boc-pyrrolidine CAS 122684-34-8
3-Aminocarbonyl-1-Boc-pyrrolidine Basic information
| Product Name: | 3-Aminocarbonyl-1-Boc-pyrrolidine |
| Synonyms: | 3-CARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;3-AMINOCARBONYL-1-BOC-PYRROLIDINE;(S)-1-BOC-PYRROLIDINE-3-CARBOXAMIDE;1-BOC-PYRROLIDINE-3-CARBOXAMIDE;TERT-BUTYL 3-(AMINOCARBONYL)PYRROLIDINE-1-CARBOXYLATE;TERT-BUTYL 3-CARBAMOYLPYRROLIDINE-1-CARBOXYLATE;1-BOC-PYRROLIDINE-3-CARBOXYAMIDE;N-[2-oxo-3-(trifluoromethyl)-3-piperidinyl]carbamic acid tert-butyl ester |
| CAS: | 122684-34-8 |
| MF: | C10H18N2O3 |
| MW: | 214.26 |
| EINECS: | |
| Product Categories: | pharmacetical |
| Mol File: | 122684-34-8.mol |
3-Aminocarbonyl-1-Boc-pyrrolidine Chemical Properties
| Melting point | 117.0 to 121.0 °C |
| Boiling point | 370.1±31.0 °C(Predicted) |
| density | 1.155±0.06 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| form | powder to crystal |
| pka | 16.40±0.20(Predicted) |
| color | White to Almost white |
| InChI | 1S/C10H18N2O3/c1-10(2,3)15-9(14)12-5-4-7(6-12)8(11)13/h7H,4-6H2,1-3H3,(H2,11,13) |
| InChIKey | NHDGOVOBEZPXMY-UHFFFAOYSA-N |
| SMILES | CC(C)(C)OC(=O)N1CCC(C1)C(N)=O |
| CAS DataBase Reference | 122684-34-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 22 |
| WGK Germany | 3 |
| HazardClass | IRRITANT |
| HS Code | 2933998090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Uses | tert-Butyl 3-Carbamoylpyrrolidine-1-carboxylate is used for preparation and sulfuration of 1,2,4-thiadiazoles. |
| Synthesis | 72925-16-7 122684-34-8 The general procedure for the synthesis of 1-BOC-pyrrolidine-3-carboxamide from (R)-1-Boc-3-carboxypyrrolidine was as follows: to a solution of 1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (5 g, 23.23 mmol) in anhydrous THF (100 mL) was added triethylamine (TEA, 4.69 g, 46.46 mmol) and isobutyl chloroformic acid ester (3.8 g, 27.87 mmol). The reaction mixture was stirred at 0 °C for 20 min. Subsequently, ammonia (NH3-H2O) was slowly added and stirring was continued for 2 h at room temperature. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 mL) and washed sequentially with saturated sodium carbonate solution (2 × 20 mL) and saturated sodium bicarbonate solution. The organic layer was then washed with citric acid solution (2 × 20 mL) to remove residual base. Finally, the organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product (2.39 g, 49% yield) as a yellow solid. Mass spectrometry (ESI) analysis showed: m/z = 159.0 [M + H]+. |
| References | [1] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 91 [2] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 2052 - 2059 [3] Chemical Biology and Drug Design, 2016, p. 54 - 65 |
3-Aminocarbonyl-1-Boc-pyrrolidine Preparation Products And Raw materials
| Raw materials | (R)-1-N-Boc-beta-proline-->Isobutyl chloroformate-->Tetrahydrofuran-->Ammonia-->Water-->Triethylamine |
| Preparation Products | 1-N-Boc-3-Cyanopyrrolidine |
