Alternatived Products of [ 6914-80-3 ]
Product Details of [ 6914-80-3 ]
| CAS No. : | 6914-80-3 |
MDL No. : | MFCD19203238 |
| Formula : |
C6H9NO3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
143.14
|
Pubchem ID : | - |
| Synonyms : |
|
Application In Synthesis of [ 6914-80-3 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 6914-80-3 ]
- 1
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[ 6914-80-3 ]
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[ 45434-02-4 ]
| Yield | Reaction Conditions | Operation in experiment |
| 79.6% |
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; |
|
|
With lithium aluminium tetrahydride In tetrahydrofuran |
|
Reference：
[1]Buchholz, Mirko; Heiser, Ulrich; Schilling, Stephan; Niestroj, André J.; Zunkel, Katrin; Demuth, Hans-Ulrich
[Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 664 - 677]
[2]Chan, Kelvin S. L.; Fu, Hai-Yan; Yu, Jin-Quan
[Journal of the American Chemical Society, 2015, vol. 137, # 5, p. 2042 - 2046]
- 2
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[ 6914-71-2 ]
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[ 6914-80-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 99% |
With ammonia; In methanol; at 20℃; for 90h; |
A solution of dimethyl cyclopropane-1 ,1 -dicarboxylate (57.8 g, 0.365 mol) in 7M ammonia in methanol was stirred at room temperature for 90 h, then evaporated under reduced pressure to afford the title compound as a colourless solid (52.2g, 99percent). H NMR (400 MHz; DMSO-d6): 7.82 (1 H, s), 7.35 (1 H, s), 3.63 (3H, s), 1 .34 (4H, s). |
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With ammonia; In methanol; |
Example (1) Preparation of Methyl 1-aminocarbonylcyclopropanecarboxylate Ammonia (20 l/h) is passed at 20° C. into a solution of 1,106 g (7 mol) of dimethyl cyclopropanedicarboxylate in 700 ml of methanol, with stirring. After approximately 10 hours, addition of NH3 is stopped, and the reaction mixture is cooled to 8° C. The solid formed is filtered off with suction, then washed using 200 g of cold methanol. After drying the product, 926.2 g (92.5percent) of methyl 1-aminocarbonylcyclopropanecarboxylate are obtained (m.p.: 157° C.). |
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With ammonia; In methanol;Inert atmosphere; |
Preparational Example 13 Preparation of 1-aminocyclopropyl acetic acid hydrochloride [0455] [0456] After reducing pressure in the reaction vessel, the vessel was filled with nitrogen gas, to which 6.8 ml of 7 N NH3 in MeOH was loaded. 1.0 g (6.30 mmol) of dimethylcyclopropane-1,1-dicarboxylate was dissolved in 63 ml of MeOH, which was also loaded into the reaction vessel. If the starting material still remained, NH3 gas could be provided for bubbling for 15 minutes. Upon completion of the reaction, the reaction solvent was eliminated by evaporation under reduced pressure and the precipitated solid compound was filtered and washed with 0° C. methanol, followed by vacuum drying. The obtained reaction product was dissolved in 5 ml of 7.4percent NaOH/H2O, followed by stirring at 40° C. for 20 minutes. Then, the temperature was lowered to room temperature (Reactant A). 7 ml of 12.3percent NaOCl and 2 ml of 30percent NaOH/H2O were stirred together at room temperature for 1 hour (Reactant B). These reactants A and B were mixed and stirred at 80° C. for 4 minutes. After lowering the temperature thereof, 4 ml of hydrochloric acid was slowly added thereto carefully not to increase the temperature more than 60° C. The solvent was eliminated by evaporation under reduced pressure and the reactant was dissolved in ethanol. The precipitated solid compound was filtered. The remaining solution was evaporated under reduced pressure and then dissolved in hot acetone. The generated solid compound was filtered and dried to give 0.5 g of 1-aminocyclopropyl acetic acid hydrochloride (yield: 58percent). [0457] 1H NMR (400 MHz, D2O) delta 1.40-1.43 (m, 2H), 1.22-1.25 (m, 2H) |
- 3
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[ 6914-80-3 ]
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[ 153248-46-5 ]
- 4
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[ 6914-80-3 ]
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[ 68781-13-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 0.5 g |
Stage #1: 1-(aminocarbonyl)-1-cyclopropanecarboxylic acid methyl ester With water; sodium hydroxide at 40℃; for 0.333333h;
Stage #2: With sodium hypochlorite; sodium hydroxide In water at 80℃; for 0.0666667h;
Stage #3: With hydrogenchloride In water at 60℃; |
P.13 Preparational Example 13 Preparation of 1-aminocyclopropyl acetic acid hydrochloride
Preparational Example 13 Preparation of 1-aminocyclopropyl acetic acid hydrochloride [0455] [0456] After reducing pressure in the reaction vessel, the vessel was filled with nitrogen gas, to which 6.8 ml of 7 N NH3 in MeOH was loaded. 1.0 g (6.30 mmol) of dimethylcyclopropane-1,1-dicarboxylate was dissolved in 63 ml of MeOH, which was also loaded into the reaction vessel. If the starting material still remained, NH3 gas could be provided for bubbling for 15 minutes. Upon completion of the reaction, the reaction solvent was eliminated by evaporation under reduced pressure and the precipitated solid compound was filtered and washed with 0° C. methanol, followed by vacuum drying. The obtained reaction product was dissolved in 5 ml of 7.4% NaOH/H2O, followed by stirring at 40° C. for 20 minutes. Then, the temperature was lowered to room temperature (Reactant A). 7 ml of 12.3% NaOCl and 2 ml of 30% NaOH/H2O were stirred together at room temperature for 1 hour (Reactant B). These reactants A and B were mixed and stirred at 80° C. for 4 minutes. After lowering the temperature thereof, 4 ml of hydrochloric acid was slowly added thereto carefully not to increase the temperature more than 60° C. The solvent was eliminated by evaporation under reduced pressure and the reactant was dissolved in ethanol. The precipitated solid compound was filtered. The remaining solution was evaporated under reduced pressure and then dissolved in hot acetone. The generated solid compound was filtered and dried to give 0.5 g of 1-aminocyclopropyl acetic acid hydrochloride (yield: 58%). [0457] 1H NMR (400 MHz, D2O) δ 1.40-1.43 (m, 2H), 1.22-1.25 (m, 2H) |
- 5
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[ 6914-80-3 ]
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[ 1123169-27-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 71% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere; |
35.2 Example 35, Step 2: 1 -(Hydroxymethyl)cyclopropanecarboxamide
Lithium aluminium hydride (27.2 g, 0.719 mol) was added portionwise over 0.75 h. to a stirred suspension of methyl 1 -carbamoylcyclopropanecarboxylate (51 .2 g, 0.358 mol) in THF (1 .5 L) at 0°C under nitrogen. On complete addition the mixture was stirred at 0°C for a further 1 .25 h. prior to dropwise addition of water (27 mL), 15% NaOH (27 mL) and water (82 mL) sequentially. The mixture was allowed to warm to room temperature, stirred for 0.5 h. and filtered through celite. The celite was washed with EtOAc and the combined filtrate and washings evaporated to give the title compound as a colourless solid (33.4 g, 71 %). H NMR (400 MHz; DMSO-d6): 7.10-6.85 (2H, m), 4.97 (1 H, t), 3.48 (2H, d), 0.90-0.85 (2H, m), 0.61 -0.58 (2H, m). |
- 6
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[ 113020-21-6 ]
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[ 6914-80-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
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To a mixture of 1 -(methoxycarbonyl)cyclopropane-1 -carboxylic acid (Int 11a) (1.00 g, 6.94 mmol) in THF (20 ml_) was added SOCI2 (1.24 g, 10.4 mmol) followed by 3 drops of DMF at 0 C. The mixture was heated to 65 C for 2 h. The mixture was concentrated to dryness, dissolved in DCM and concentrated to dryness for a second time. The residue was added portion wise to a mixture of concentrated aqueous NFUOFI (5 ml_) and TFIF (20 ml_) at 0 C. The precipitated solid was filtered off, washed with water and dried under reduced pressure to give the title compound. |
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