Phenethylamine → (S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1668419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668419
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[CH2:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:12]([C:17](=[O:19])[NH:39][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:13][CH2:14][C:15]1=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Produkt 1

HCID 57612752(S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

(S)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (14.9 g, 57 mmol) is suspended in dichloromethane (100 mL) and added DMAP (7.1 g, 58 mmol) while cooling on ice (0-5° C.). The suspension immediately clarified. EDCI (11.1 g, 58 mmol) is added resulting in precipitation which quickly clarified again. Phenethylamine (6.8 mL, 54 mmol) is added slowly via syringe. The reaction is complete in one half hour. The dichloromethane layer is washed with aqueous 10% citric acid, water and saturated bicarb, then dried over anhydrous sodium sulfate, filtered and concentrated to a white solid. LCMS characterization ES+367.1 (m+1).

Aufarbeitung

  1. customresulting in precipitation which
  2. waitThe reaction is complete in one half hour
  3. washThe dichloromethane layer is washed with aqueous 10% citric acid, water and saturated bicarb
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a white solid

Quellen und Nachweise

ORD-Eintrag
ord-4f1e8a73cb34449180ba72306e66a5ab
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989441B2

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