Alternatived Products of [ 263409-78-5 ]
Product Details of [ 263409-78-5 ]
CAS No. : | 263409-78-5 |
MDL No. : | MFCD24393200 |
Formula : |
C13H18FNO3
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
255.29
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 263409-78-5 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 263409-78-5 ]
* 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.
- Upstream synthesis route of [ 263409-78-5 ]
- Downstream synthetic route of [ 263409-78-5 ]
- 1
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[ 371-41-5 ]
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[ 26690-80-2 ]
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[ 263409-78-5 ]
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[ 97308-23-1 ]
- 2
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[ 263409-78-5 ]
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[ 6096-89-5 ]
Yield | Reaction Conditions | Operation in experiment |
71.6% |
With trifluoroacetic acid; In dichloromethane; at 20℃; for 12h; |
To a solution of tert-butyl (2-(4-fluorophenoxy)ethyl)carbamate (0.3 g, 1.175 mmol) in DCM (6 mL) was added 2,2,2-trifluoroacetic acid (1 mL, 13.46 mmol) at once. The reaction mixture was stirred at room temperature for 12 h. The solvents were removed in vacuo, water (10 mL) was added to the solid with stirring and the pH value was adjusted to 8 with sat NaHC03 The mixture was extracted with DCM (20 mL x3), washed with water (50 mL), then organic layer was dried over NaiSOr and concentrated to afford a brown oil which was purified by chromatography on silica gel eluting with pet. Ether : EtOAc (5: 1) to give desired product 2-(4-fluorophenoxy)ethanamine (150 mg, 0.841 mmol, 71.6 % yield) as yellow solid. LCMS (M+H) = 156, Retention time (0.01% TFA) = 1.13. |
|
With trifluoroacetic acid; at 0℃; for 0.5h; |
Dissolve (2- (4-fluorophenoxy) ethyl) carbamic acid tert-butyl ester (435 mg, 2.28 mmol) in trifluoroacetic acid (5 mL) cooled in an ice bath and stirred for 30 minutes. Reduce the solution in vacuo and dissolve in pyridine (10 mL) along with acetic anhydride (1. 1 mL, 11.0 mmol). After 18 hours remove the solvent under vacuum. Dissolve the residue in dichloromethane and first extract with saturated sodium bicarbonate solution followed by a IN HCI solution extraction. Dry and reduce the organic layer to give 272 mg of a solid that is N- (2- (4-FLUOROPHENOXY) ethyl) acetamide which is carried without purification to the next step. Mix the N- (2- (4- fluorophenoxy) ethyl) acetamide (240 mg, 1.22 mmol) with Lawesson's reagent (296 mg, 0.73 mmol) in toluene and heat at 80C for 90 minutes. Remove the solvent IN VACUO to give an oil. Dissolve the oil in ether and remove the solid precipitate by filtration. Add excess iodomethane (3 mL) and leave at room temperature for 17 hours. Reduce in vacuo to give an oil. Dissolve the oil in dichloromethane and wash with saturated sodium bicarbonate solution. Dry and reduce the solution to give 92 mg (0.405 mmol) OF N- (2- (4-fluorophenoxy) ethyl) thioacetimidic acid methyl ester as an oil. Dissolve this product in dichloromethane and add trifluoromethanesulfonic acid methyl ester (90. 5 UL, 0.8 mmol). After 18 hours remove the solvent to give an oil (129 mg). Dissolve this oil in pyridine and add (R)- (6-AMINO-2 (R)-HYDROXYINDAN-L-YL) carbamic acid tert-butyl ester (87 mg, 0.33 mmol). After 24 hours remove the solvent in vacuo to give an oil. Dissolve the oil in dichloromethane and wash with saturated sodium bicarbonate solution. Dry the organic layer and reduce under vacuum to give 88.9 mg of the titled compound and use as is. |
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