Lithium Hydroxide → 1-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid

HRID 490630

Reaktionsgleichung

Reaktionsgleichung von HRID 490630
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=2)[CH2:7][N:6]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[CH2:26]([N:6]1[CH2:7][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[C:14]([C:22]([F:25])([F:23])[F:24])[CH:13]=2)[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 86625300Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester

Produkt 1

HCID 866253011-Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

Benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid methyl ester (124 mg, 0.269 mmol) and LiOH (53.9 mg, 1.5 mmol) were dissolved in THF/H2O (4 mL), and then stirred overnight. After removal of solvent, the residue was neutralized to PH=6-7, and then extracted by EA twice. The organic layer was washed with water and brine, dried, and concentrated to afford the title product 1-benzyl-4-(3,5-bis-trifluoromethyl-benzylamino)-pyrrolidine-2-carboxylic acid, 65 mg (54.2%) as a yellow solid. MS m/e=447.3 [M+H]+.

Aufarbeitung

  1. customAfter removal of solvent
  2. extractionextracted by EA twice
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3a71e5dcb9244f36b75b8f6ae1ccb9b0
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528136B2

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