Hydrochloric Acid → HCID 22270492, Verbindung

HRID 30374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30374
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10](=[N:12]O)[CH3:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.CCOCC>[ClH:1].[NH2:12][CH:10]([CH:9]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:11]

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 21226445Aluminium lithium hydrideHCID 858679314-(4-Chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one Oxime

Produkt 1

HCID 22270492HCID 22270492, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

At room temperature, to a solution of 4-(4-chlorophenyl)-3-pyrrolidin-N-yl-butan-2-one oxime (173 mg, 0.648 mmol, from Step C) in 1.8 mL anhydrous THF was added dropwise a 1M solution of lithium aluminum hydride in THF (0.778 mmole). The mixture was refluxed for 20 h. The reaction was quenched by addition of saturated aqueous sodium sulfate (0.1 mL), and stirred overnight. This mixture was filtered over a pad of CELITE diatomaceous earth, and the filtrate was concentrated to dryness. The mass spectrum of this material looked very messy, so the HCl salt was prepared (by addition of a HCl(g) in ether solution) in attempt to clean up the mess. By NMR, the reductive amination provided a ˜1:1 mixture of the two diastereomeric pairs of amines. This HCl salt was rather sticky and difficult to work with and therefore was used in the ensuing coupling experiment without further purification. LC/MS m/e=253 (M+1). 500 MHz 1H NMR (CD3OD) δ 1.56, 1.59 (2 d, J=7.2 Hz, 3H), 2.03 (m, 6H), 2.08 (m, 2H), 3.204.00 (m, 3H), 7.43 (m, 4H)

Aufarbeitung

  1. temperatureThe mixture was refluxed for 20 h
  2. customThe reaction was quenched by addition of saturated aqueous sodium sulfate (0.1 mL)
  3. filtrationThis mixture was filtered over a pad of CELITE diatomaceous earth
  4. concentrationthe filtrate was concentrated to dryness
  5. customwas prepared (
  6. customBy NMR, the reductive amination provided
  7. customtherefore was used in the ensuing coupling experiment without further purification

Quellen und Nachweise

ORD-Eintrag
ord-fa062d37e8464d1095b5c653a0b89413
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423067B2

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