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2,2-Dimethylpropane-1-sulfonyl chloride → 1-(2,2-Dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2194015
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2194015
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:16][C:17]([CH3:24])([CH3:23])[CH2:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:7][CH2:8][N:9]([S:19]([CH2:18][C:17]([CH3:24])([CH3:23])[CH3:16])(=[O:21])=[O:20])[CH2:10][CH2:11]1)=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 125746322,2-Dimethylpropane-1-sulfonyl chlorideHCID 567539694-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Produkt 1

HCID 667872401-(2,2-Dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.72 g) in methylene chloride (40 ml) was added at RT under an argon atmosphere DMAP (0.75 g) and then dropwise 2,2-dimethyl-propane-1-sulfonyl chloride (0.57 ml). The reaction mixture was stirred 12 h at RT then partitioned between AcOEt and aqueous 1M HCl, the layers were separated and the aqueous layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, the residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 40%) to give the desired 1-(2,2-dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.34 g) as a light yellow viscous oil.

Aufarbeitung

  1. customthen partitioned between AcOEt and aqueous 1M HCl
  2. customthe layers were separated
  3. washthe aqueous layer washed with 2M aqueous KHCO3
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent was evaporated off
  6. customthe residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 40%)

Quellen und Nachweise

ORD-Eintrag
ord-3a7af084099446a8802f671448494d85
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08329904B2

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