1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

HRID 1359740

Reaktionsgleichung

Reaktionsgleichung von HRID 1359740
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=N[CH2:24][CH2:25][CH2:26][N:27]([CH3:29])C.C1C=CC2N(O)N=NC=2C=1.N1CCCC1>CN(C=O)C.O.C(=O)(O)[O-].[Na+]>[CH2:4]([O:3][C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13]([N:27]1[CH2:26][CH2:25][CH2:24][CH2:29]1)=[O:15])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 667614(R)-Benzyl 2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of (+)-carbobenzyloxy-D-proline (1.5 g, 6 mmol), EDAC (2.3 g, 12 mmol), HOBt (800 mg, 6 mmol), TEA (1.5 mL) and pyrrolidine (853 mg, 12 mmol) in DMF (20 mL) was stirred at rt for 18 hours. The reaction was diluted with water and sodium bicarbonate, extracted with DCM (3×). The combined DCM was concentrated and purified on a silica gel column to give (R)-2-(pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester.

Aufarbeitung

  1. extractionextracted with DCM (3×)
  2. concentrationThe combined DCM was concentrated
  3. custompurified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-5f9f8fbc16794791adcba827f64da92a
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599902B2

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