Aluminium lithium hydride → HCID 178432775, Verbindung

HRID 1914667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914667
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[C:15]([CH3:21])=[N:16][CH:17]=[C:18]([Cl:20])[CH:19]=2)=[O:13])[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:20][C:18]1[CH:17]=[N:16][C:15]([CH3:21])=[C:14]([CH:19]=1)[C:12]([NH:11][C@H:8]1[CH2:7][CH2:6][C@H:5]([CH2:3][OH:2])[CH2:10][CH2:9]1)=[O:13]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 178501231HCID 178501231, Verbindung

Produkt 1

HCID 178432775HCID 178432775, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trans-4-[(5-Chloro-2-methyl-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid methyl ester (step 2) (2.20 g, 7.08 mmol) is placed in a flask with dry THF (100 mL). This is cooled to 0° C. and lithium aluminum hydride (0.537 g, 14.16 mmol) is added. The reaction mixture is stirred at r.t. for 2 hours and then quenched with water (0.5 mL), 2M NaOH (0.5 mL) and then water again (1.5 mL). The solids are filtered off through Celite® (filter material) and the filtrate is partitioned between EtOAc and water. The organic phase is washed with water and brine, dried over MgSO4, filtered and the solvent is removed in vacuo to afford the title product which is used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (1H, d), 8.38*1H, d), 7.79 (1H, d), 4.40 (1H, t), 3.66 (1H, m), 3.21 (2H, t), 2.47 (3H, s), 1.92 (2H, m), 1.78 (2H, m), 1.31 (1H, m), 1.22 (2H, m), 0.98 (2H, m). [MH]+283.30.

Aufarbeitung

  1. customquenched with water (0.5 mL), 2M NaOH (0.5 mL)
  2. filtrationThe solids are filtered off through Celite® (filter material)
  3. customthe filtrate is partitioned between EtOAc and water
  4. washThe organic phase is washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d87d6a686899470cbac8b43231dbcbed
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614213B2

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