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CAS No.: | 37088-66-7 |
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Name: | METHYL (3S)-3-AMINO-3-PHENYLPROPANOATE |
Article Data: | 39 |
Molecular Structure: | |
Formula: | C10H13NO2 |
Molecular Weight: | 179.219 |
Synonyms: | methyl (3S)-3-amino-3-phenylpropanoate;Methyl (S)-3-amino-3-phenylpropanoate; |
Density: | 1.098±0.06 g/cm3(Predicted) |
Boiling Point: | 283.0±28.0 °C(Predicted) |
PSA: | 52.32000 |
LogP: | 1.94980 |
(Z)-3-amino-3-phenylacrylic acid methyl ester
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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With di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium; [1'-P(4-CF3Ph)2-2'-(R)-CH(Me)-P(t-Bu)2]ferrocene; hydrogen In 2,2,2-trifluoroethanol at 50℃; under 5171.48 Torr; for 6h; | 97.6% |
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; Josiphos-7 at 50℃; under 5931.67 Torr; | 92 %Chromat. |
methanol
(S)-3-amino-3-phenylpropanoic acid
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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With thionyl chloride Heating; | 95% |
With hydrogenchloride In water for 16h; Heating / reflux; | 84% |
sulfuric acid for 24h; Heating / reflux; | 65% |
methyl (S)-3-(benzhydrylamino)-3-phenylpropionate
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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With hydrogen; palladium on activated charcoal In methanol at 25℃; under 760 Torr; for 2.5h; Catalytic hydrogenation; | 95% |
methyl 3-oxo-3-phenylpropionate
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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Stage #1: methyl 3-oxo-3-phenylpropionate With Ru(OAc)2((R)-dm-segphos); hydrogen; ammonium salicylate In methanol at 85℃; under 22502.3 Torr; for 7h; Autoclave; Stage #2: With sodium carbonate In water; ethyl acetate for 0.5h; optical yield given as %ee; enantioselective reaction; | 84% |
With ammonium acetate; hydrogen; Ru(OCOCH3)2((R)-dm-binap) In methanol at 80℃; under 22502.3 Torr; for 16h; | 40% |
Multi-step reaction with 2 steps 1: NH4OAc / methanol / 5 h / Heating 2: 97.6 percent / [(COD)RhCl]2; H2; [1'-P(4-CF3Ph)2-2'-(R)-CH(Me)-P(t-Bu)2]ferrocene / 2,2,2-trifluoro-ethanol / 6 h / 50 °C / 5171.48 Torr View Scheme | |
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / methanol / Reflux 2: (S)-(2-(bis(3,3-dimethylphenyl)(hydroxy)methyl)pyrrolidin-1-yl)(pyridin-2-yl)methanone; trichlorosilane / chloroform / 48 h / -30 °C 3: ammonium cerium (IV) nitrate; water / acetonitrile / 0 - 20 °C View Scheme |
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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With trifluoroacetic acid In methanol at 0℃; for 2h; | 73% |
(S)-methyl 3-(4-methoxyphenylamino)-3-phenylpropanoate
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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With ammonium cerium (IV) nitrate; water In acetonitrile at 0 - 20℃; optical yield given as %ee; | 65% |
methyl (S)-3-amino-3-phenylpropanoate L-(+)-tartaric acid salt
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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In methanol at 20℃; Inert atmosphere; Reflux; Large scale; | 63% |
With sodium hydroxide; water | 0.30 g |
methyl (3S)-3-[(1R)-N-(4-methoxybenzyl)-1-(4-methoxyphenyl)ethylamino]-3-phenylpropanoate
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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Stage #1: methyl (3S)-3-[(1R)-N-(4-methoxybenzyl)-1-(4-methoxyphenyl)ethylamino]-3-phenylpropanoate With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 17h; Stage #2: With hydrogenchloride In methanol at 60℃; for 2h; | 60% |
methyl 3-amino-3-phenylacrylate
(3S)-methyl 3-amino-3-phenylpropanoate
Conditions | Yield |
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With hydrogen; chloroacetic acid; Ru(OCOCH3)2((R)-H8-binap) In methanol at 50℃; under 22502.3 Torr; for 88h; Product distribution / selectivity; | 39.5% |
With hydrogen; Ru(OCOCH3)2((S)-dm-binap) In methanol at 50℃; under 22502.3 Torr; for 88h; Product distribution / selectivity; | 9% |
methyl 3-amino-3-phenylpropanoate
(3S)-methyl 3-amino-3-phenylpropanoate