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Imidazole → 4-((alphaS)-alpha-((2R,5R)-2,5-dimethyl-4-propyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-N,N-diethylbenzamide

HRID 1038627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038627
[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([C@@H:11]([C:19]2[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[C@H:6]([CH3:32])[CH2:5]1)[CH:2]=[CH2:3].C1(O)C=CC=CC=1.[C:40]([Si:44](Cl)([CH3:46])[CH3:45])([CH3:43])([CH3:42])[CH3:41].N1C=CN=C1>C1(C)C=CC=CC=1.C(#N)C.O>[CH3:32][C@@H:6]1[CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[C@H:9]([CH3:10])[CH2:8][N:7]1[C@@H:11]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([N:25]([CH2:26][CH3:27])[CH2:28][CH3:29])=[O:24])=[CH:30][CH:31]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si:44]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:46])[CH3:45])[CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 795ImidazoleHCID 996PhenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 10238234HCID 10238234, Verbindung

Produkt 1

HCID 186650764-((alphaS)-alpha-((2R,5R)-2,5-dimethyl-4-propyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-N,N-diethylbenzamideAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(−)-4-((αS)-α-((2R,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide (0.200 g, 0.46 mmol, Example 2) was dissolved in toluene (10 mL) and stirred for 4 hours under a hydrogen atmosphere. The solution was filtered through celite to give 0.182 g of crude product. The phenol was reprotected as follows to improve chromatographic resolution. A mixture of crude product (0.18 g), tert-butylchlorodimethylsilane (0.93 g), and imidazole (0.070 g) in 10 mL of acetonitrile was stirred overnight at room temperature. The reaction solution was poured into 100 mL of water and extracted with two 50 mL portions of dichloromethane. The combined extracts were dried over sodium sulfate and the solvent removed. The residue was purified on a column of silica gel with ethanol (0-4%) in dichloromethane to give 0.085 g of 4-((αS)-α-((2R,5R)-2,5-dimethyl-4-propyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-N,N-diethylbenzamide as a light-brown solid.

Aufarbeitung

  1. filtrationThe solution was filtered through celite
  2. customto give 0.182 g of crude product
  3. stirringwas stirred overnight at room temperature
  4. extractionextracted with two 50 mL portions of dichloromethane
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. customthe solvent removed
  7. customThe residue was purified on a column of silica gel with ethanol (0-4%) in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-985fd1ef6e6840978bf283c21925a8d2
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08551998B2

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