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Basic Information
| CAS No.: | 357336-20-0 |
|---|---|
| Name: | brivaracetam |
| Article Data: | 50 |
| Molecular Structure: | |
|
|
|
| Formula: | C11H20 N2 O2 |
| Molecular Weight: | 212.292 |
| Synonyms: | Brivaracetam;UCB 34714 |
| Density: | 1.062 |
| Melting Point: | 76.38° |
| Boiling Point: | 409.3±28.0 °C(Predicted) |
| PSA: | 63.40000 |
| LogP: | 1.53710 |
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Synthetic route
- 357338-13-7
(2S)-4,5-dehydro-(2-oxo-4-n-propyl-1-pyrrolidinyl)-2-butanamide
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; copper(l) chloride; sodium t-butanolate In toluene at -40℃; for 24h; Inert atmosphere; | 99.3% |
| With 5% Pd-CaCO3; hydrogen In methanol; water at -10 - 0℃; Temperature; Reagent/catalyst; Solvent; | 70.2% |
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With potassium tert-butylate In tetrahydrofuran | 93% |
| With sodium hydroxide In dichloromethane at -15 - -10℃; Concentration; Reagent/catalyst; Temperature; Solvent; | 90% |
| With lithium hexamethyldisilazane In tetrahydrofuran at -15 - -5℃; for 4h; | 69.8% |
- 53726-14-0
(S)-2-amino-butanamide hydrochloride
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With sodium carbonate In ethanol at 50℃; for 24h; Temperature; | 93% |
- 7324-11-0, 53726-14-0, 104652-77-9, 143164-46-9
(S)-2-amino-butanamide
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: C7H13IO2 With 1,1'-carbonyldiimidazole In toluene at 10 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: (S)-2-amino-butanamide In toluene at 10 - 20℃; | 92% |
- 7324-11-0, 53726-14-0, 104652-77-9, 143164-46-9
(S)-2-amino-butanamide
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate In ethanol at 60℃; for 8h; Reagent/catalyst; Solvent; Temperature; | 91% |
| With tetra-(n-butyl)ammonium iodide; sodium carbonate In Isopropyl acetate at 88.8℃; for 28h; Inert atmosphere; Cooling; | 32% |
| Stage #1: (S)-2-amino-butanamide; ethyl (R)-γ-bromo-3-propylbutyrate With tetra-(n-butyl)ammonium iodide; sodium carbonate In Isopropyl acetate for 28h; Reflux; Stage #2: With acetic acid In Isopropyl acetate at 60℃; for 1.83h; | 12.66% |
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With ammonium chloride; N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 2h; Time; Large scale; | 90% |
| With ammonia; pivaloyl chloride; triethylamine In dichloromethane at 0 - 10℃; for 6h; Inert atmosphere; | 88% |
| Stage #1: (2S)-2-[(4R)-2-oxo-4-n-propyl-1-pyrrolidinyl]butyric acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -10 - -5℃; for 1h; Stage #2: With ammonium bicarbonate In dichloromethane at -10 - -5℃; | 67% |
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| In isopropyl alcohol for 6h; Reflux; | 89.3% |
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; ammonia In water at 5℃; under 750.075 - 1125.11 Torr; for 15h; | 88.7% |
- 7324-11-0, 53726-14-0, 104652-77-9, 143164-46-9
(S)-2-amino-butanamide
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With potassium hydroxide In dichloromethane at 0 - 5℃; for 2h; Molecular sieve; | 87% |
- 357336-20-0
brivaracetam
Conditions
| Conditions | Yield |
|---|---|
| With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 15h; | 86.4% |
| With ammonium hydroxide; ammonia In water at 5℃; under 750.075 - 1125.11 Torr; for 15h; | 34 g |
| With ammonia In tetrahydrofuran at 20℃; for 20h; | 0.91 g |
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