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Ammonium Chloride → tert-butyl (3R,5S)-3-(1-hydroxycyclohexyl)-5-[(2-methylpropyl)amino]piperidine-1-carboxylate

HRID 2192840
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2192840
[CH3:1][CH:2]([CH3:22])[CH2:3][NH:4][C@@H:5]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C@H:7]([C:18]([O:20]C)=O)[CH2:6]1.[CH2-:23][CH2:24][CH2:25][CH2:26][CH2-:27].[Mg+2].[Mg+2].[Br-].[Br-].[Cl-].[NH4+]>C1COCC1>[OH:20][C:18]1([C@@H:7]2[CH2:6][C@H:5]([NH:4][CH2:3][CH:2]([CH3:1])[CH3:22])[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:8]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 3637391Pentamethylene-1,5-bis(magnesium bromide)HCID 593566071-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

Produkt 1

HCID 59625268tert-butyl (3R,5S)-3-(1-hydroxycyclohexyl)-5-[(2-methylpropyl)amino]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

1-tert-Butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (3.0 g) was dissolved in THF (30 ml), a solution (15.2 ml) of 3 M pentamethylenebis(magnesium bromide) in THF was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 3 hr. 2 N Aqueous ammonium chloride solution (50 ml) was added to the reaction solution under ice-cooling, and the mixture was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:10→10:0) was concentrated under reduced pressure to give the object compound (1.3 mg).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe fraction eluted with ethyl acetate-hexane (0:10→10:0)
  7. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2a090ec2e8a748bd9e823450418f2231
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329691B2

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