3,5-Bis(trifluoromethyl)benzaldehyde → HCID 86648399, Verbindung

HRID 409461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409461
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH:21]=O.[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:21][C:20]2[CH:23]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:25]=[C:18]([C:17]([F:16])([F:30])[F:31])[CH:19]=2)[CH2:10][C@H:9]1[CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 59614425HCID 59614425, Verbindung

Produkt 1

HCID 86648399HCID 86648399, VerbindungAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (2R,4S)-4-amino-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (150 mg, 0.7 mmol) in methanol (2 mL) is added to 3,5-bis-trifluoromethyl-benzaldehyde (340 mg, 1.4 mmol), and the reaction mixture is stirred at room temperature. After stirring for overnight, sodium borohydride (53 mg, 1.4 mmol) is added. After stirring for additional 1 hour, The product is extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give crude (2R,4S)-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (250 mg).

Aufarbeitung

  1. stirringAfter stirring for overnight
  2. stirringAfter stirring for additional 1 hour
  3. extractionThe product is extracted three times with EtOAc
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-af3fd20455734c2aa6219a5e92a54305
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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