Sodium hydride → HCID 53773441, Verbindung

HRID 482084

Reaktionsgleichung

Reaktionsgleichung von HRID 482084
[OH:1][C:2]1[CH:3]=[C:4]([O:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].CS(O[CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]1)(=O)=O>CN(C=O)C.C(OCC)(=O)C>[C:36]([O:35][C:33]([N:29]1[CH2:30][CH2:31][CH2:32][CH:27]([CH2:26][O:1][C:2]2[CH:3]=[C:4]([O:8][S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH2:28]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 22647269tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylateHCID 540152812-Chlorobenzenesulfonic acid 3-hydroxyphenyl ester

Produkt 1

HCID 53773441HCID 53773441, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-chlorobenzenesulfonic acid 3-hydroxyphenyl ester (570 mg, 2.0 mmol), as prepared in step d of Example 1, in DMF (8 mL) was added NaH (95%, 53 mg, 2.2 mmol). The reaction mixture was stirred under nitrogen for 10 min. N-(tert-Butoxycarbonyl)-3-piperidinemethanol methanesulfonate (586 mg, 2.0 mmol), as prepared in step b, was added and the reaction mixture was stirred at 40° C. under nitrogen overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (2:1 hexane:ethyl acetate) to give the title compound as a colorless syrup (510 mg, 54%). 1H-NMR (300 MHz, CDCl3) δ 1.32 (m, 1H), 1.45 (s, 9H), 1.65-1.98 (m, 4H), 2.88 (m, 2H), 3.73 (m, 2H), 3.79 (d, 2H), 6.69 (m, 2H), 7.13 (t, 1H), 7.37 (t, 1H), 7.61 (m, 2H), 7.94 (d, 1H).

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 40° C. under nitrogen overnight
  3. washwashed sequentially with saturated NaHCO3 (2×50 mL) and brine (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (2:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-903f408b3d434577a52f9b0d826dff02
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792769

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