p-Toluenesulfonate → HCID 178486035, Verbindung

HRID 25644

Reaktionsgleichung

Reaktionsgleichung von HRID 25644
[C:1]([O:5][C:6](=[O:26])[N:7]([CH3:25])[C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]#[C:15][CH2:16][CH2:17][O:18]C2CCCCO2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1>CO>[C:1]([O:5][C:6](=[O:26])[N:7]([C@H:8]1[CH2:9][CH2:10][C@H:11]([C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH2:12][CH2:13]1)[CH3:25])([CH3:2])([CH3:4])[CH3:3]

Komponenten

4

Edukt 2

HCID 85570p-ToluenesulfonateHCID 178486034HCID 178486034, Verbindung

Produkt 1

HCID 178486035HCID 178486035, VerbindungAusbeute 107,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3.45 g (9.44 mmol) of trans-Methyl-{4-[4-(tetrahydro-pyran-2-yloxy)-but-1-ynyl]-cyclohexyl}-carbamic acid tert-butyl ester and 0.7 g (2.83 mmol) of pyrimidium toluene-4-sulfonate in 25 ml MeOH was stirred at 55° C. for 1.5 h. The reaction was partitioned between aqueous solution of 10% KHSO4/ether (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl, dried over Na2SO4 and evaporated to give 2.85 g (quantitative) of trans-[4-(4-Hydroxy-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 281 (M).

Aufarbeitung

  1. customThe reaction was partitioned between aqueous solution of 10% KHSO4/ether (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3be0d935e22a48a8b35edee8c35950cd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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