- Methods for making optically active 3-aminopyrrolidine-2,5-dione derivative and optically active 3-aminopyrrolidine derivative
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A method for making an optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) includes cyclizing an optically active asparagine ester derivative represented by the formula (1) or (2), or an acid salt thereof. A method for making an optically active 3-aminopyrrolidine derivative represented by the formula (9) includes reducing the optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3). A method for making an optically active 3-aminopyrrolidine derivative includes hydrogenolyzing the optically active 3-aminopyrrolidine derivative represented by the formula (9).
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Page column 13
(2008/06/13)
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- Methods for making optically active 3-aminopyrrolidine-2,5-dione derivative and optically active 3-aminopyrrolidine derivative
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A method for making an optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) includes cyclizing an optically active asparagine ester derivative represented by the formula (1) or (2) or an acid salt thereof. The optically active 3-aminopyrrolidine-2,5-dione derivative represented by the formula (3) may be reduced to form an optically active 3-aminopyrrolidine derivative represented by the formula (9). When, in the formula (9), R1 is an unsubstituted or substituted benzyl group, the compound may be hydrogenated to obtain the corresponding 1-unsubstituted compound in which R1 is hydrogen.
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- Process for producing 1H-3-aminopyrrolidine and derivatives thereof
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A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino
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- Process for producing 1H-3-aminopyrrolidine and derivatives thereof
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A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R'NH2, subjecting the reaction product to cyclodehydration to obtain an optically active 1-aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.
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- Handy access to chiral N,N'-disubstituted 3-aminopyrrolidines
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A new and rapid synthesis of (S)-3-aminopyrrolidines Z is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the
- Maddaluno,Corruble,Leroux,Ple,Duhamel
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p. 1239 - 1242
(2007/10/02)
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