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Sodium hydride → [(2S)-4-methylmorpholin-2-yl]methyl 4-(2,4-difluorophenyl)-piperazine-1-carboxylate

HRID 2262495
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2262495
[CH3:1][N:2]1[CH2:7][CH2:6][O:5][C@H:4]([CH2:8][OH:9])[CH2:3]1.[H-].[Na+].[N+](C1C=CC([O:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])[CH2:26][CH2:25]2)=O)=CC=1)([O-])=O>C1COCC1>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[N:27]1[CH2:28][CH2:29][N:24]([C:22]([O:9][CH2:8][C@H:4]2[O:5][CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]2)=[O:21])[CH2:25][CH2:26]1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 40152302(S)-4-Methyl-2-(hydroxymethyl)morpholine2×HCID 533966704-nitrophenyl 4-(2,4-difluorophenyl)tetrahydro-1(2H)-pyrazinecarboxylate2×

Produkt 1

HCID 42634188[(2S)-4-methylmorpholin-2-yl]methyl 4-(2,4-difluorophenyl)-piperazine-1-carboxylateAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

(S)-(4-Methylmorpholin-2-yl)-methanol (Intermediate 10; 100 mg, 0.76 mmol) was added to a suspension of NaH (60% dispersion in oil; 90.0 mg, 2.28 mmol) in anhydrous THF (7 mL) and stirred under nitrogen for 30 min. 4-(2,4-Difluorophenyl)-piperazine-1-carboxylic acid 4-nitrophenyl ester (Intermediate 12, 330 mg, 0.91 mmol) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction mixture was filtered through celite and the solid washed with THF (10 mL). The filtrates were combined and the solvent removed in vacuo. The residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM) and the solvents were removed in vacuo to give [(2S)-4-methylmorpholin-2-yl]methyl 4-(2,4-difluorophenyl)-piperazine-1-carboxylate (104 mg, 38%) as a colourless gum.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 48 h
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe solid washed with THF (10 mL)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM)
  6. customthe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-80288d586dce482d8b88006dd64a6f7c
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851471B2

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