Efficient synthesis of N-benzyl-3-aminopyrrolidine-2,5-dione and N-benzyl-3-aminopyrrolidin-2-one

Tetrahedron Letters

Volumn 45, Issue 18, 2004, Pages 3603-3605

  Vo Hoang, Yen ^a   Gasse, Cécile ^a   Vidal, Michel ^b   Garbay, Christiane ^b   Galons, Hervé ^a  

^a Faculte de Pharmacie   (France)

^b Laboratoire de Pharmacochimie   (France)

Author keywords

Aminopyrrolidinedione; Aminopyrrolidinone; Aminosuccinimide; Cyclic imide

Indexed keywords

3 TERT BUTYLOXYCARBONYLAMINOPYRROLIDIN 2 ONE; 3 TERT BUTYLOXYCARBONYLAMINOPYRROLIDINE 2,5 DIONE; ASPARAGINE DERIVATIVE; BENZYL BROMIDE; BORANE DERIVATIVE; BORANE DIMETHYLSULFIDE; CARBONIC ACID DERIVATIVE; CESIUM CARBONATE; KETONE DERIVATIVE; N BENZYL 3 AMINOPYRROLIDIN 2 ONE; N BENZYL 3 AMINOPYRROLIDINE 2,5 DIONE; N BENZYL 3 TERT BUTYLOXYCARBONYLAMINOPYRROLIDINE 2,5 DIONE; N TERT BUTYLOXYCARBONYLASPARAGINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 1842736587     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.052     Document Type: Article

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21. 1=17.5 Hz), 4.16 (m, 1H), 4.62 (s, 2H), 5.11 (s, 1H), 6.93 (d, 2H, J=8.0 Hz), 7.32 (d, 2H, J=8.0 Hz). To avoid the preparation of cesium carbonate salt in hydromethanolic solution, we developed an alternative procedure: cesium carbonate (0.853 g, 2.63 mmol) was added to Boc-Asn (0.205 g, 0.88 mmol) in 5 mL of DMF. The mixture was stirred for 2 days at room temperature to complete the salt formation. Then benzyl bromide (42 μL, 2.2 mmol) was added. After stirring for 6 h at room temperature, the same treatment was applied. 1-Benzyl-3-Bocaminosuccinimide 1a, was isolated in a similar yield.
22. 3CN.
23. -1.
24. 3) δ (ppm): 2.12 (m, 1H), 2.40 (m, 1H), 3.25 (m, 2H), 4.05 (t, 1H, J=9 Hz), 4.31 (d, 1H J=15 Hz), 4.38 (d, 1H J=15 Hz), 7.20-7.35 (m, 5H), 8.4 (br s, 3H).