Reaktion #7278

Reaktionsgleichung

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N-(tert-butoxycarbonyl)-L-proline

N,N-diisopropylethylamine

1-hydroxybenzotriazole hydrate

1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl

→

amide

Ausbeute 116.9%

(S)-Pyrrolidine-2-carboxylic acid 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzylamide

Ausbeute 116.9%

Lösungsmittel

CH2Cl2

sodium bicarbonate

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe aqueous layer was separated
2. 2
   Extraktionextracted with CH2Cl2 (2×15 mL)
3. 3
   TrocknenThe combined organic phases were dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigeto give the crude product as a white foam
7. 7
   SonstigePurification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4)

Vorschrift

To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (148 mg, 0.37 mmol) in dry CH2Cl2 (5 mL) was added N-(tert-butoxycarbonyl)-L-proline (88 mg, 0.41 mmol), N,N-diisopropylethylamine (0.13 mL, 0.75 mmol), 1-hydroxybenzotriazole hydrate (68 mg, 0.50 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (EDC) (99 mg, 0.52 mmol) and the mixture stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (25 mL) and saturated aqueous sodium bicarbonate (30 mL) and the aqueous layer was separated and extracted with CH2Cl2 (2×15 mL). The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to give the crude product as a white foam. Purification by column chromatography on silica gel (CH2Cl2/MeOH, 96:4) gave the desired amide (214 mg, 85%) as a white foam.

Quelle