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Name |
(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-hydroxy(phenyl)ethanoate |
EINECS | 1308068-626-2 |
CAS No. | 376608-71-8 | Density | N/A |
PSA | 83.55000 | LogP | 3.28430 |
Solubility | N/A | Melting Point |
N/A |
Formula | C9H9F2N.C8H8O3 | Boiling Point | N/A |
Molecular Weight | 321.324 | Flash Point | N/A |
Transport Information | N/A | Appearance | N/A |
Safety | 24/25 | Risk Codes | N/A |
Molecular Structure | Hazard Symbols | N/A | |
Synonyms |
(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium (2R)-hydroxy(phenyl)ethanoate;(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanaminium; |
Article Data | 11 |
trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid With pyridine; thionyl chloride In toluene at 70℃; for 4h; Stage #2: With sodium azide; tetrabutylammomium bromide; sodium carbonate In water; toluene at 0℃; for 2h; Stage #3: (R)-Mandelic Acid In ethyl acetate at 17 - 25℃; for 3h; | 82% |
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
In Isopropyl acetate at 0 - 20℃; for 4h; | 70.1% |
In methanol at 20 - 25℃; for 14h; | 46.4% |
In methanol at 20 - 25℃; for 12h; |
trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane
(R)-Mandelic Acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane With hydrogenchloride; zinc In methanol; water at -5 - 0℃; Stage #2: With ammonia In dichloromethane; water at 30℃; for 0.25h; Stage #3: (R)-Mandelic Acid In methanol at 20 - 25℃; | 36.61% |
Stage #1: trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane With hydrogenchloride; zinc In deuteromethanol at -5 - 0℃; Stage #2: (R)-Mandelic Acid In methanol at 0 - 25℃; for 14h; | 36.61% |
ortho-difluorobenzene
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 4 h / 20 - 25 °C / Industry scale 2.1: sodium iodide; 3,5-dihydroxyphenol; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / toluene / 25 - 40 °C / Inert atmosphere 4.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 5.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 5.2: 0.25 h / 30 °C 5.3: 20 - 25 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: aluminum (III) chloride / dichloromethane / 30 h / 20 - 25 °C / Industry scale 2.1: sodium iodide; sodium azide; 3,5-dihydroxyphenol / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 5.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 5.2: 0.25 h / 10 - 30 °C 6.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / dichloromethane / 20 - 25 °C / Large scale 2.1: sodium nitrite; 3,5-dihydroxyphenol; sodium iodide / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 3.1: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 25 - 30 °C / Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 5.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 5.2: 14 h / 0 - 25 °C View Scheme |
3-chloro-1-(3',4'-difluorophenyl)-propan-1-one
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium iodide; 3,5-dihydroxyphenol; sodium nitrite / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / toluene / 25 - 40 °C / Inert atmosphere 3.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 4.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 4.2: 0.25 h / 30 °C 4.3: 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium iodide; sodium azide; 3,5-dihydroxyphenol / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 4.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 4.2: 0.25 h / 10 - 30 °C 5.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium nitrite; 3,5-dihydroxyphenol; sodium iodide / N,N-dimethyl-formamide / 5 - 30 °C / Inert atmosphere 2.1: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 25 - 30 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 4.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 4.2: 14 h / 0 - 25 °C View Scheme |
1-(3',4'-difluorophenyl)-3-nitro-propan-1-one
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane N,N-diethylaniline complex / toluene / 25 - 40 °C / Inert atmosphere 2.1: triphenylphosphine / toluene / 2 h / 0 - 10 °C 3.1: hydrogenchloride; zinc / water; methanol / -5 - 0 °C 3.2: 0.25 h / 30 °C 3.3: 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; borane Ν,Ν-diethylaniline complex / toluene / 1.5 h / 15 - 20 °C / Inert atmosphere 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 3.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 3.2: 0.25 h / 10 - 30 °C 4.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: borane Ν,Ν-diethylaniline complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 25 - 30 °C / Inert atmosphere 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 3.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 3.2: 14 h / 0 - 25 °C View Scheme |
(1S)-1-(3,4-difluorophenyl)-3-nitropropan-1-ol
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 5 - 10 °C 2.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 2.2: 0.25 h / 10 - 30 °C 3.1: methanol / 12 h / 20 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / 2 h / 0 - 10 °C 2.1: hydrogenchloride; zinc / deuteromethanol / -5 - 0 °C 2.2: 14 h / 0 - 25 °C View Scheme |
trans-(1R,2S)-2-(3,4-difluorophenyl)-1-nitrocyclopropane
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; zinc / methanol / -5 - 0 °C 1.2: 0.25 h / 10 - 30 °C 2.1: methanol / 12 h / 20 - 25 °C View Scheme |
(E)-methyl 3-(3,4-difluorophenyl)acrylate
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 25 °C 1.2: 16 h / 0 - 25 °C 2.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 3.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 4.1: toluene / 1 h / 110 °C 4.2: 2 h / 100 °C 4.3: 25 °C / pH 10 5.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
(E)-3-(3,4-difluorophenyl)acrylic acid
trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2R)-2-hydroxy-2-phenylacetic acid salt
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sulfuric acid / 72 h / 60 °C 2.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 25 °C 2.2: 16 h / 0 - 25 °C 3.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 4.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 5.1: toluene / 1 h / 110 °C 5.2: 2 h / 100 °C 5.3: 25 °C / pH 10 6.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: oxalyl dichloride / dichloromethane / 0 h / 25 - 30 °C 1.2: 0 h / 25 - 30 °C 2.1: pyridine / acetone / 0 h / 0 - 30 °C 2.2: 0 - 5 °C 3.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 3.2: 3 h / 25 - 30 °C 4.1: hydrazine hydrate / methanol / 12 h / 60 - 65 °C 5.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 6.1: toluene / 1 h / 110 °C 6.2: 2 h / 100 °C 6.3: 25 °C / pH 10 7.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: oxalyl dichloride / dichloromethane / 0 h / 25 - 30 °C 1.2: 0 h / 25 - 30 °C 2.1: pyridine / acetone / 0 h / 0 - 30 °C 2.2: 0 - 5 °C 3.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 3.2: 3 h / 25 - 30 °C 4.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C 6.1: hydrazine hydrate / 1,4-dioxane / 3 h / 65 °C 7.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 8.1: toluene / 1 h / 110 °C 8.2: 2 h / 100 °C 8.3: 25 °C / pH 10 9.1: methanol / 2.5 h / 18 - 45 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: oxalyl dichloride / dichloromethane / 0 h / 25 - 30 °C 1.2: 0 h / 25 - 30 °C 2.1: pyridine / acetone / 0 h / 0 - 30 °C 2.2: 0 - 5 °C 3.1: sodium hydride / dimethyl sulfoxide / 1 h / 25 - 30 °C 3.2: 3 h / 25 - 30 °C 4.1: hydrogenchloride / 1,4-dioxane / 16 h / 25 - 30 °C 5.1: sulfuric acid / 2 h / 60 °C 6.1: hydrazine / water; methanol / 16 h / 25 - 70 °C 7.1: sodium nitrite; acetic acid / 0.5 h / 25 °C 8.1: toluene / 1 h / 110 °C 8.2: 2 h / 100 °C 8.3: 25 °C / pH 10 9.1: methanol / 2.5 h / 18 - 45 °C View Scheme |
(1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine is an intermediate in the preparation of orally active reversible P2Y12 receptor antagonists for the prevention of thrombosis.