Water → trans-(2-{4-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol

HRID 32230

Reaktionsgleichung

Reaktionsgleichung von HRID 32230
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:14][CH:13]1[CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH:28]2[CH2:33][C:32]([CH3:35])([CH3:34])[CH2:31][C:30]([CH3:37])([CH3:36])[CH2:29]2)[CH2:18][CH2:17]1)=O)C.[F-].[Na+].O>O1CCCC1>[CH3:36][C:30]1([CH3:37])[CH2:31][C:32]([CH3:34])([CH3:35])[CH2:33][CH:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:19]2[CH2:20][CH2:21][N:16]([CH2:15][C@H:13]3[CH2:14][C@H:12]3[CH2:10][OH:9])[CH2:17][CH2:18]2)[CH2:29]1.[CH3:36][C:30]1([CH3:37])[CH2:31][C:32]([CH3:34])([CH3:35])[CH2:33][CH:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:19]2[CH2:20][CH2:21][N:16]([CH2:15][C@@H:13]3[CH2:14][C@H:12]3[CH2:10][OH:9])[CH2:17][CH2:18]2)[CH2:29]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 5235Sodium FluorideHCID 21226445Aluminium lithium hydrideHCID 597694042-{4-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropanecarboxylic acid ethyl ester

Produkt 2

HCID 59769446trans-(2-{4-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanolHCID 69219555cis-(2-{4-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (178 mg, 4.68 mmol) was suspended in anhydrous tetrahydrofuran (15 mL), and the suspension was stirred at room temperature under a nitrogen atmosphere. To the suspension was added a solution of 2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropanecarboxylic acid ethyl ester (1 g, 2.34 mmol) produced in Example (91) in anhydrous tetrahydrofuran (15 mL), followed by stirring for 1 hour and 30 minutes at room temperature. Sodium fluoride (1 g) was added to the reaction mixture, and water (0.4 mL) was gradually added while blowing nitrogen. After stirring for 1 hour, the insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane). This procedure gave 173 mg of cis-(2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol as colorless crystals, and 596 mg of trans-(2-{4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazin-1-ylmethyl}cyclopropyl)methanol as a colorless oil.

Aufarbeitung

  1. stirringby stirring for 1 hour and 30 minutes at room temperature
  2. additionwas gradually added
  3. stirringAfter stirring for 1 hour
  4. filtrationthe insoluble materials were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-04a4ce15e710426abdd95fbc8f46cf6b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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