Lithium diisopropylamide → 1-tert-butyl 4-ethyl 4-((1-trityl-1H-imidazol-4-yl)methyl)piperidine-1,4-dicarboxylate

HRID 216077

Reaktionsgleichung

Reaktionsgleichung von HRID 216077
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.Cl[CH2:28][C:29]1[N:30]=[CH:31][N:32]([C:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=1>C1COCC1>[C:34]([N:32]1[CH:33]=[C:29]([CH2:28][C:4]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:6][CH2:5]2)[N:30]=[CH:31]1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

5

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 27631764-(Chloromethyl)-1-trityl-1H-imidazole

Produkt 1

HCID 670377361-tert-butyl 4-ethyl 4-((1-trityl-1H-imidazol-4-yl)methyl)piperidine-1,4-dicarboxylateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (360 mg, 1.39 mmol) in anhydrous THF (10 mL) at −78° C. was added LDA (1.7 M in THF, 1.07 mL, 1.8 mmol) dropwise over 10 min. The reaction mixture was stirred at −78° C. for 1 hour, and 4-(chloromethyl)-1-trityl-1H-imidazole (500 mg, 13.9 mmol) in THF (5 mL) was added slowly. The reaction mixture was allowed to warm to room temperature over 1 hour, quenched with sat. aq. NH4Cl (10 mL), and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum. Purification by silica gel chromatography (10-50% EtOAc:Hexanes) afforded the title compound (403 mg, 51%). MS (ES+) [M+H]+=580.3.

Aufarbeitung

  1. temperatureto warm to room temperature over 1 hour
  2. customquenched with sat. aq. NH4Cl (10 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification by silica gel chromatography (10-50% EtOAc:Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a686ec2fdb7548279e6c96c348001610
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193202B2

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